Chapter 5

Stereochemistry Chiral Chi l Molecules l l

Created by Professor William Tam & Dr. Phillis Chang

Ch. 5 - 1

About The Authors

These Powerpoint Lecture Slides were created and prepared by Professor William Tam and his wife Dr. Phillis Chang. Professor William Tam received his B.Sc. at the University of Hong Kong in 1990 and his Ph.D. at the University of Toronto (Canada) in 1995. He was an NSERC postdoctoral fellow at the Imperial College (UK) and at Harvard University (USA). He joined the Department of Chemistry at the University of Guelph (Ontario, Canada) in 1998 and is currently a Full Professor and Associate Chair in the department. Professor Tam has received several awards in i research and teaching, and according to E h dt hi d di t Essential Science Indicators, h is ti l S i I di t he i currently ranked as the Top 1% most cited Chemists worldwide. He has published four books and over 80 scientific papers in top international journals , g , g , g such as J. Am. Chem. Soc., Angew. Chem., Org. Lett., and J. Org. Chem. Dr. Phillis Chang received her B.Sc. at New York University (USA) in 1994, her M.Sc. and Ph.D. in 1997 and 2001 at the University of Guelph (Canada). She lives in Guelph with her husband, William, and their son, Matthew. li i G l h ith h h b d Willi d th i M tth

Ch. 5 - 2

1. Chirality & Stereochemistry

An object is achiral (not chiral) if the object and its mirror image are identical

Ch. 5 - 3

A chiral object is one that cannot be superposed on its mirror image d it i i

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1A. The Biological Significance of Chirality

Chiral molecules are molecules that cannot be superimposable with their mirror images
O N O

O Thalidomide

One enantiomer causes birth defects, NH O the other cures morning sickness

Ch. 5 - 5

HO HO Tretoquinol OMe NH OMe OMe

One enantiomer is a bronchodilator, the other inhibits platelet aggregation

Ch. 5 - 6

66% of all drugs in development are chiral, chiral 51% are being studied as a single enantiomer Of the $475 billion in world-wide sales of formulated pharmaceutical products in 2008, $205 billion was attributable to single enantiomer drugs

Ch. 5 - 7

2. Isomerisom: Constitutional Isomers & S I Stereoisomers i

2A. 2A Constitutional Isomers

Isomers: different compounds that p have the same molecular formula Constitutional isomers: isomers that have the same molecular formula but different connectivity their atoms are connected in a different order
Ch. 5 - 8

Examples Constitutional Isomers

and d Butane 2-Methylpropane
Cl

Molecular Formula C4H10

C3H7Cl

Cl 1-Chloropropane

and 2-Chloropropane
Ch. 5 - 9

Examples Constitutional Isomers

CH3 O CH3 OH and Ethanol Methoxymethane
O

Molecular Formula C2H6O

C4H8O2

OH and Butanoic acid

OCH3 O Methyl propanoate

Ch. 5 - 10

2B. Stereoisomers

Stereoisomers are NOT constitutional isomers Stereoisomers have their atoms connected in the same sequence but q they differ in the arrangement of their atoms in space. The consideration of such spatial aspects of molecular structure is called stereochemistry
Ch. 5 - 11

2C. Enantiomers & Diastereomers

Stereoisomers can be subdivided into two general categories: enantiomers & diasteromers Enantiomers stereoisomers whose molecules are nonsuperposable mirror images of each other Diastereomers stereoisomers whose molecules are not mirror images of each other Ch. 5 - 12

Geometrical isomers (cis & t i trans i isomers) are: ) Diastereomers

e.g. Ph Ph and Ph Ph

(cis)
Cl H Cl and H H

(trans)
Cl H Cl

(cis)

(trans)
Ch. 5 - 13

Subdivision of Isomers
(different compounds with same molecular formula)

Isomers

Constitutional Isomers
(isomers whose atoms have a different connectivity) diff t ti it )

(isomers that have the same connectivity but differ in spatial arrangement of their atoms)

Stereoisomers

(stereoisomers that are nonsuperposable mirror images of each other)

Enantiomers

(stereoisomers that are NOT mirror images of each other)

Diastereomers

Ch. 5 - 14

3. Enantiomers and Chiral Molecules M l l

Enantiomers occur only with compounds whose molecules are chiral A chiral molecule is one that is NOT superposable on its mirror image Th relationship between a chiral The l ti hi b t hi l molecule and its mirror image is one that is enantiomeric. A chiral molecule and its mirror image are said to be enantiomers of each other

Ch. 5 - 15

OH

(2-Butanol)

H () (I)

OH

HO

H ( ) (II)

(I) and (II) are nonsuperposable mirror images of each other h th

Ch. 5 - 16

4. A Single Chirality Center Causes a M l C Molecule to Be Chi l l B Chiral

The most common type of chiral compounds that we encounter are molecules that contain a carbon atom l l th t t i b t bonded to four different groups. Such a carbon atom is called an asymmetric carbon or a chiral center and is usually designated with an asterisk (*)
Ch. 5 - 17

Cl Me C* Et H
H

Cl

Cl Et

H Me (IV)

Me Et (III)

mirror i

(III) and (IV) are nonsuperposable mirror images of each other

Ch. 5 - 18

Cl Me C Me H
H Me (V)

Cl Me

Cl Me mirror i

Me (VI)

(V) and (VI) are superposable not enantiomers achiral

Ch. 5 - 19

4A. Tetrahedral vs. Trigonal Stereogenic Centers

Chirality centers are tetrahedral stereogenic centers

H OH

HO

Tetrahedral stereogenic center chiral

Me * Et (A)

Et * Me (B) mirror

(A) & (B) are enantiomers ti

Ch. 5 - 20

Cis and trans alkene isomers contain

trigonal stereogenic centers
Ph H (C) H Ph

H Ph (D) mirror

Ph H

Trigonal stereogenic center achiral

(C) & (D) are identical

Ch. 5 - 21

4A. Tetrahedral vs. Trigonal Stereogenic Centers

Chirality centers are tetrahedral stereogenic centers

Cis and trans alkene isomers contain

trigonal stereogenic centers

Ch. 5 - 22

5. More about the Biological Importance of Chi li I f Chirality

(+) Limonene (+)-Limonene (limonene enantiomer found in oranges)

( ) Limonene (-)-Limonene (limonene enantiomer found in lemons)

Ch. 5 - 23

Thalidomide

The activity of drugs containing chirality centers can vary b t hi lit t between enantiomers, sometimes with serious or even tragic consequences For several years before 1963 thalidomide was used to alleviate the symptoms of morning sickness in pregnant women t
Ch. 5 - 24

In 1963 it was discovered that thalidomide (sold as a mixture of both enantiomers) was the cause of horrible birth defects in many children born subsequent to the use of the drug
O O O N O NH O O N NH O

Thalidomide (cures morning sickness) ( g )

O enantiomer of Thalidomide (causes birth defects)

Ch. 5 - 25

6. How to Test for Chirality: Planes of S Pl f Symmetry

A molecule will not be chiral if it possesses a plane of symmetry A plane of symmetry (mirror plane) is an imaginary plane that bisects a molecule g yp such that the two halves of the molecule are mirror images of each other All molecules with a plane of symmetry in their most symmetric conformation are achiral Ch. 5 - 26

Plane of symmetry
Me

Cl Me H

achiral hi l

Cl Me H Et

No plane of symmetry

chiral

Ch. 5 - 27

7.

Naming Enantiomers: R,S-System

OH H (I) OH HO H (II)

Recall:

Using only the IUPAC naming that we have learned so f these two enantiomers will l d far, h ll have the same name: 2-Butanol This is undesirable because each compound must have its own distinct name
Ch. 5 - 28

7A. How to Assign (R) and (S) Configurations

Rule 1 Assign priorities to the four different groups on the stereocenter from highest to lowest (priority bases on atomic number, the higher the atomic number, the higher the , g priority)
Ch. 5 - 29

Rule 2 When a priority cannot be assigned on the basis of the atomic number of the atoms that are directly attached to the chirality center, then h d h hi li h the next set of atoms in the unassigned groups is examined. This process is continued until a decision can be made.
Ch. 5 - 30

Rule 3 Visualize the molecule so that the lowest priority group is directed away from you, then trace a path from hi h f highest to lowest priority. If l i i f the path is a clockwise motion, then the configuration at the asymmetric carbon is (R). If the path is a counter-clockwise motion, then the configuration is (S)
Ch. 5 - 31

Example

HO

(2-Butanol)

Step 1:
or

or

Step 2:

H3C

(H, H, H)

C CH 3 C H2

(C, H, H)

Ch. 5 - 32

OH Et
H

OH

Me M

Et Me OH
HO H Et = H

OH Me Et

Me

Arrows are clockwise

Et Me

(R) 2 )-2-Butanol l
Ch. 5 - 33

Other examples
Cl

Cl

Counterclockwise

H HO

CH3

HO O

C CH3

(S)
Clockwise

OCH3
CH2CH3

OCH3 Br

H3 C

Br

(R)
Ch. 5 - 34

CH2CH3

Other examples
Rotate CCl bond such that H is pointed to the back
Cl Br HO

Cl

Br

OH
Cl

Clockwise

Br

OH

(R)
Ch. 5 - 35

Other examples
Rotate CCH3 bond such that H is p pointed to the back
H I H3C

OCH3

OCH3

H I H3C

Counter clockwise Counter-clockwise

OCH3 I

H3C

(S)
Ch. 5 - 36

Rule 4 F groups containing double or For t i i d bl triple bonds, assign priorities as if both atoms were duplicated or triplicated p
e.g.
C O as C O O C C C C C C C C C C C

C C

as

C C

as

Ch. 5 - 37

Example

CH3

H HO

(S)

CH=CH CH CH2

Compare C

CH3

&

CH CH2 : H H C C H C C

CH CH2 Thus, CH3

equivalent to

(H, H, H)

CH CH2 (C, C, H)
Ch. 5 - 38

Other examples

OH

(R)
CH3

Cl O
H2C

OH
CH3 C (O, O, C)

H
Cl

(S)

C (O, H, H)
Ch. 5 - 39

8.

Properties of Enantiomers: Optical Activity

Enantiomers Mirror images that are not superposable bl

H Cl H3CH2C
*

H
*

CH3 mirror

H3C

Cl CH2CH3
Ch. 5 - 40

Enantiomers have identical physical properties (e.g. melting point, boiling ti ( lti i t b ili point, refractive index, solubility etc.)
Compound bp (oC) 99.5 99.5 168 170 168 170 210 212
Ch. 5 - 41

mp (oC)

(R)-2-Butanol (S)-2-Butanol ) 2 Butanol (+)-(R,R)-Tartaric Acid ()-(S,S)-Tartaric Acid (+/)-Tartaric Acid

Enantiomers Have the same chemical properties (except reaction/interactions with chiral substances) Sh Show different b h i only when diff behavior l h they interact with other chiral substances Turn plane polarized light on plane-polarized opposite direction
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Optical activity The property possessed by chiral substances of rotating the plane of polarization of plane-polarized light

Ch. 5 - 43

8A. Plane-Polarized Light Plane-

The electric field (like the magnetic field) of light is osc at g in a e d) o g t s oscillating all possible planes When this light passes through a polarizer (Polaroid lens), we get planepolarized light (oscillating in only one l i d li ht ( ill ti i l plane)

Polaroid lens l
Ch. 5 - 44

8B. The Polarimeter

A device for measuring the optical activity of a chiral compound

=observed observed optical rotation

Ch. 5 - 45

8C. Specific Rotation

temperature observed b d rotation
25

[ ] []D =
wavelength g of light ( g (e.g. D-line of Na lamp, =589.6 nm) 589 6 )

concentration length of cell in dm of sample solution (1 dm = 10 cm) in g/mL

Ch. 5 - 46

The value of depends on the particular experiment (since there are different concentrations with each run) But specific rotation [] should be the same regardless of the concentration t ti

Ch. 5 - 47

Two enantiomers should have the same value of specific rotation, b t th l f ifi t ti but the signs are opposite
CH3 H HO
25

CH3
*

CH2CH3
o

H3CH2C
25

H OH
o

[] = + 13.5
D

mirror

[] = 13.5
D

Ch. 5 - 48

9.

The Origin of Optical Activity

Ch. 5 - 49

Ch. 5 - 50

Two circularlyy polarized beams g counter-rotating at the same velocity ( p (in phase), and ), their vector sum

Two circularly-polarized yp beams counter-rotating , at different velocities, such as after interaction , with a chiral molecule, and their vector sum
Ch. 5 - 51

9A. Racemic Forms A equimolar mixture of two An i l i t ft enantiomers is called a racemic mixture (or racemate or racemic form) A racemic mixture causes no net rotation of plane-polarized light
rotation equal & opposite q pp rotation by the enantiomer

CH3

OH C2H5

H HO C2H5 (S)-2-Butanol (if present)

Ch. 5 - 52

H3C

(R)-2-Butanol

9B. Racemic Forms and Enantiomeric Excess

A sample of an optically active substance that consists of a single enantiomer i said to be ti is id t b enantiomerically pure or to have an enantiomeric excess of 100%

Ch. 5 - 53

An enantiomerically pure sample of (S)-(+)2-butanol 2 butanol shows a specific rotation of +13.52

[] [ ]D

25 5

= +13.52

A sample of (S)-(+)-2-butanol that contains less than an equimolar amount of (R) ( ) l h l f )-()-2butanol will show a specific rotation that is less than 13.52 but greater than zero l h b h Such a sample is said to have an enantiomeric excess less than 100%
Ch. 5 - 54

Enantiomeric excess (ee) Al known as the optical purity Also k th ti l it

mole of one enantiomer moles of other enantiomer x 100

% enantiomeric = excess

total moles of both enantiomers

Can be calculated from optical rotations

% enantiomeric = excess * observed specific rotation specific rotation of the p pure enantiomers x 100

Ch. 5 - 55

Example A mixture of th 2 b t i t f the 2-butanol l enantiomers showed a specific rotation of +6.76. The enantiomeric excess of the (S)-(+)( )( ) 2-butanol is 50%
+6.76 +13.52 x 100 = 50%

% enantiomeric = excess *

Ch. 5 - 56

10. The Synthesis of Chiral Molecules 10A. Racemic Forms

Ni ( )-CH3CH2CHCH3 OH Hydrogen (achiral molecules) l l ) ( )-2-Butanol (chiral molecules; b l l but 50:50 mixture (R) & (S))
Ch. 5 - 57

CH3CH2CCH3 + H H O Butanone (achiral molecules) l l )

Ch. 5 - 58

10B.

Stereoselective Syntheses

Stereoselective reactions are reactions p that lead to a preferential formation of one stereoisomer over other stereoisomers that p y could possibly be formed enantioselective if a reaction p produces preferentially one enantiomer p y over its mirror image diastereoselective if a reaction leads preferentially to one diastereomer over others that are possible p
Ch. 5 - 59

O OEt F racemate ( )

H , H2O heat h t

O OH + EtOH F racemate ( )

O OEt F racemate ( )

H2O lipase

O OH F () ( ) (> 69% ee) O + OEt + EtOH F (+) (> 99% ee)

Ch. 5 - 60

11. Chiral Drugs

Of the $475 billion in world-wide sales of formulated pharmaceutical products in 2008, $205 billion was attributable to single enantiomer drugs
HO O NMe2 HO NH3 CO2 H

NC

Escitalpram (anti-depressant )

L-DOPA L DOPA (treatment for Parkinson's)

Ch. 5 - 61

Naproxen (anti-inflammatory (anti inflammatory drug)

CO2H CH3

MeO

NaO2C S Cl N

CH3 HO CH3

Singulair (asthma and allergy treatment)

Ch. 5 - 62

12. Molecules with More than One Chirality Center

Diastereomers Stereoisomers that are not enantiomers Unlike enantiomers, diastereomers usually have substantially different y y chemical and physical properties
Ch. 5 - 63

(I)

Br Cl C H HO C H CH3

Br H C Cl OH H C CH3 Br H C Cl H C CH3 OH

(II)

Br Cl C H (III) CH3 C H HO

(IV)

Note: I compounds with n tetrahedral N In d ih h d l stereocenters, the maximum number of stereoisomers is 2n.
Ch. 5 - 64

(I)

Br Cl C H HO C H CH3

Br H C Cl OH H C CH3 Br H C Cl H C CH3 OH

(II)

Br Cl C H (III) CH3 C H HO

(IV)

(I) & (II) are enantiomers to each other (III) & (IV) are enantiomers to each other

Ch. 5 - 65

(I)

Br Cl C H HO C H CH3

Br H C Cl OH H C CH3 Br H C Cl H C CH3 OH

(II)

Br Cl C H (III) CH3 C H HO

(IV)

Diastereomers to each other: (I) & (III), (I) & (IV), (II) & (III), (III) (IV) (III) (II) & (IV)

Ch. 5 - 66

12A.

Meso Compounds

Compounds with two stereocenters do not always have four stereoisomers (22 = 4) since some molecules are achiral (not chiral), even though they chiral) contain stereocenters F example, 2 3 di hl For l 2,3-dichlorobutane has b t h two stereocenters, but only has 3 stereoisomers (not 4)
Ch. 5 - 67

(I)

CH3 C Br CH3 C Br H H

Br Br

H C CH 3 (II) C CH3 H H C CH 3 (IV) C H CH3

CH3 C Br (III) H C Br CH3

Br Br

Note: (III) contains a plane of symmetry, N i l f is a meso compound, and is achiral ([] = 0o).
Ch. 5 - 68

(I)

CH3 C Br CH3 C Br H H

Br Br

H C CH 3 (II) C CH3 H H C CH 3 (IV) C H CH3

CH3 C Br (III) H C Br CH3

Br Br

(I) & (II) are enantiomers to each other and chiral (III) & (IV) are identical and achiral

Ch. 5 - 69

(I)

CH3 C Br CH3 C Br H H

Br Br

H C CH 3 (II) C CH3 H H C CH 3 (IV) C H CH3

CH3 C Br (III) H C Br CH3

Br Br

(I) & (III), (II) & (III) are diastereomers (III) di Only 3 stereoisomers: y (I) & (II) {enantiomers}, (III) {meso}
Ch. 5 - 70

12B. How to Name Compounds with More than One Chirality Center

2,3 Dibromobutane 2 3-Dibromobutane

Br
1

Br
3 4
a

Look through C2Ha bond

Br C2: (R) configuration

H
2

C1

C3

(H, H, H) (Br, C, H)
Ch. 5 - 71

 Look through C3Hb bond

H Br
a

Br
2 1 3

Br
C4
3

CH3

C2

CH3

(H, H, H) (Br, C, H)
C3: (R) configuration

F ll name: Full

( , ) , (2R, 3R)-2,3-Dibromobutane
Ch. 5 - 72

13. Fischer Projection Formulas

13A. How To Draw and Use Fischer Projections

Fischer Projection
COOH Ph OH CH3
Ch. 5 - 73

HO

Et

Br

COOH
Ph

Br Et t CH3

Ph O OH

Br B Et

H3C

COOH

H Ph

Me COOH H OH
COOH
H Ph

Me OH

COOH

COOH HO H

Fischer Me Projection P j ti

HO

H H Ph

Me Ph

H
Ch. 5 - 74

H H3C

Cl

Cl CH3

Cl H3C

Cl

H CH3

(I) (2S, 3S)-Dichlorobutane

CH3 H Cl CH3 Cl H

(II) (2R, 3R)-Dichlorobutane

CH3

enantiomers
mirror

Cl H CH3

H Cl

(I) and (II) are both chiral and they are d b th hi l d th enantiomers with each other Ch. 5 - 75

Cl H3C

CH3 Cl CH3 H H CH3 Cl Cl

(III) (2S, 3R) Dichlorobutane )-Dichlorobutane

Plane of symmetry

(III) is achiral (a meso compound) i hi l ( d) (III) and (I) are diastereomers to each ( ) () other
Ch. 5 - 76

14. Stereoisomerism of Cyclic Compounds C d

a meso compound
mirror H Me Me H H Me Me H

achiral
Me H Me H

enantiomers

Plane of symmetry

Ch. 5 - 77

14A. Cyclohexane Derivatives 1 4 Di 1,4-Dimethylcyclohexane h l l h

Me

Plane of symmetry

Me

Me

Me

Both cis- & trans1,4-dimethylcyclohexanes are achiral and optically inactive p y

H

Me Me H Me

The cis & trans Me forms are

H cis-1,4-dimethyl cyclohexane

H trans-1,4-dimethyl cyclohexane

diastereomers
Ch. 5 - 78

1,3-Dimethylcyclohexane
Plane of symmetry

Me

Me

Me H H (meso) Me

cis-1,3-dimethyl
cyclohexane

cis-1,3-Dimethylcyclohexane has a plane of symmetry and is a meso compound Ch. 5 - 79

1,3-Dimethylcyclohexane
NO plane of symmetry
Me * * Me
Me H Me H Me H H Me

trans-1,3-dimethyl
cyclohexane

enantiomers

trans-1,3-Dimethylcyclohexane exists as a pair of enantiomers i i f i

Ch. 5 - 80

1,3-Dimethylcyclohexane H t Has two chirality centers b t only hi lit t but l three stereoisomers
cis-1,3-dimethyl
cyclohexane Me H H Me

trans-1,3-dimethyl
cyclohexane Me H H H Me Me H Me

(meso)

enantiomers
Ch. 5 - 81

1,2-Dimethylcyclohexane
mirror
H Me Me H enantiomers H Me Me H

trans-1,2-Dimethylcyclohexane exists as a pair of enantiomers i i f i

Ch. 5 - 82

1,2-Dimethylcyclohexane With cis-1,2-dimethylcyclohexane i 1 2 di th l l h the situation is quite complicated

mirror
Me H Me M () (I) H Me H Me M H ( ) (II)

(I) and (II) are enantiomers to each other h

Ch. 5 - 83

 However, (II) can rapidly be interconverted t (III) by a ring flip i t t d to b i fli

2' 1'

Me M

mirror

Me M H 2 Me
1

H Me

() (I)

( ) (II)

Me Me
2 1

(III)

Ch. 5 - 84

 Rotation of (III) along the vertical axis gives (I) i i

2' 1'

Me H Me

Me H 2 Me
1

(I)

(II)

C1 of (II) and (III) become C2 of (I) & C2 of (II) and (III) become C1 of (I)

Me

Me

(III)
Ch. 5 - 85

2' 1'

Me H Me

Me H 2 Me
1

(I)

(II)

Although (I) and (II) are enantiomers to each other, they can interconvert rapidly i t t idl (I) and (II) are

Me

Me

(III)

achiral

Ch. 5 - 86

15. Relating Configurations through Reactions in Which No Bonds to the Chirality Center Are Broken

If a reaction takes place in a way so that no bonds to the chirality center are broken, the product will of necessity have the same general configuration of groups around the g g p chirality center as the reactant
Ch. 5 - 87

Same configuration
O Me H H NaBH4 MeOH OH H H Me H

Me Ph

H Br

NaCN DMSO

Me Ph

H CN

Same configuration

Ch. 5 - 88

15A. Relative and Absolute Configurations Chi lit centers in different molecules have Chirality t i diff t l l h the same relative configuration if they share three groups in common and if these h th i d th groups with the central carbon can be superposed in a pyramidal arrangement di id l t
Y X A B II C A B I C The chirality centers in I and II have the same relative configuration. Their common groups and central carbon can be superposed. Ch. 5 - 89

The absolute configuration of a chirality center is its (R) or (S) designation, which designation can only be specified by knowledge of the actual arrangement of groups in space at the chirality center

(R)-2-Butanol

(S)-2-Butanol

HO H
enantiomers

H OH
Ch. 5 - 90

16. Separation of Enantiomers: Resolution R l i

e.g. eg

Resolution separation of two enantiomers

O OH R * R' (racemic) O Cl OMe Ph CF3 (Mosher acid chloride) hl id ) R O R' OMe CF3 Ph O

+
R

O R'

OMe CF3 Ph

(1

1)

diastereomers usually separable either by flash column chromatography or recrystallization etc.

Ch. 5 - 91

Kinetic Resolution
OH R * R1 OH R * R1 R2 OH

R *

R1 O R2

R2 (racemic)

One enantiomer reacts fast and fast another enantiomer reacts slow

Ch. 5 - 92

e.g.
t

Me3Si

BuOOH, Ti(O Pr)4 (-)-DET

HO

Me3Si OH + C5H11

Me3Si O OH

OH

C5H11 (racemic)
(-)-DET:

COOEt COOEt

C5H11

HO

(D)-(-)-Diethyl Tartrate (D) ( ) Di th l T t t

42% (99%ee)

43% (99%ee)

Me3Si R' S OH H Me3Si H R OH R'

* stop reaction at 50% * maximum yield = 50%

Ch. 5 - 93

17. Compounds with Chirality Centers O h than C b C Other h Carbon

R4 R1 Si R3 R2 R4 R1 N R3 R2 X H R1 Ge R3 R2 R2 S R1 O

Ch. 5 - 94

18. Chiral Molecules That Do Not Possess a Chi li C P Chirality Center

P(Ph)2 P(Ph)2 (S) BINAP )-BINAP (Ph)2P (Ph)2P (R) BINAP )-BINAP

enantiomers

Ch. 5 - 95

mirror H C Cl C C H Cl H Cl H C C C Cl

enantiomers

Ch. 5 - 96

 END OF CHAPTER 5

Ch. 5 - 97