Resolution of Enantiomers

Separation of a racemic mixture into its two

respective enantiomers
Properties of Diastereomers
Diastereomers have different physical properties, so they can be easily
separated.
Enantiomers differ only in reaction with other chiral molecules and the
direction in which polarized light is rotated.
Enantiomers are difficult to separate.
Convert enantiomers into diastereomers to be able to separate them.

Resolution of Enantiomers

React the racemic mixture with a pure chiral compound, such as

tartaric acid, to form diastereomers, then separate them.

Chromatographic
Resolution of Enantiomers

Prochirality
a molecule is prochiral if it can become chiral in a single chemical step
sp2 carbons are designated: Re (similar to R) or Si (similar to S)

sp3 hybridized carbon atoms

Prochiral center
Becomes chiral by changing one attached group
Consider the following:

pro-R: replaced atom leads to R configuration

pro-S: replaced atom leads to S configuration

Prochiral distinctions, paired atoms or groups

An sp3 carbon with two groups that are the same is a prochirality center
The two identical groups are distinguished by considering either and
seeing if it was increased in priority in comparison with the other
If the center becomes R the group is pro-R and pro-S if the center
becomes S

Prochiral distinctions, paired atoms or groups

An sp3 carbon with two groups that are the same is a
prochirality center
The two identical groups are distinguished by considering
either and seeing if it was increased in priority in
comparison with the other
If the center becomes R the group is pro-R and pro-S if the
center becomes S

Prochiral Distinctions in Nature

Biological reactions often involve making distinctions
between prochiral faces or or groups
Chiral entities (such as enzymes) can always make such a
distinction
Example: addition of water to fumarate

Questions: Identify the indicated Hs as Pro R or Pro S

Questions: Identify the indicated faces as Re or Si

Questions:

Lactic acid in tired muscles results from reduction (addition of H) of

pyruvate from the Re face. What is the stereochemistry of the product?