Enantioselective synthesis

In the Sharpless dihydroxylation reaction the chirality of the product can be controlled by the "AD-mix" used. This is an example of enantioselective synthesis using asymmetric induction

Key: RL = Largest substituent; RM = Medium-sized substituent; RS = Smallest substituent
Two enantiomers of a generic alpha amino acid
  Carbon at the chiral center
  Carboxylic acid group
  R group
  Hydrogen

Enantioselective synthesis, also called asymmetric synthesis,[1] is a form of chemical synthesis. It is defined by IUPAC as "a chemical reaction (or reaction sequence) in which one or more new elements of chirality are formed in a substrate molecule and which produces the stereoisomeric (enantiomeric or diastereomeric) products in unequal amounts."[2]

Put more simply: it is the synthesis of a compound by a method that favors the formation of a specific enantiomer or diastereomer. Enantiomers are stereoisomers that have opposite configurations at every chiral center. Diastereomers are stereoisomers that differ at one or more chiral centers.

Enantioselective synthesis is a key process in modern chemistry and is particularly important in the field of pharmaceuticals, as the different enantiomers or diastereomers of a molecule often have different biological activity.

  1. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "asymmetric synthesis". doi:10.1351/goldbook.A00484
  2. ^ IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "stereoselective synthesis". doi:10.1351/goldbook.S05990