Aldol Reaction - Stereoselectivity

Stereoselectivity

The aldol reaction is particularly useful because two new stereogenic centers are generated in one reaction. Extensive research has been performed to understand the reaction mechanism and improve the selectivity observed under many different conditions. The syn/anti convention is commonly used to denote the relative stereochemistry at the α- and β-carbon.

The convention applies when propionate (or higher order) nucleophiles are added to aldehydes. The R group of the ketone and the R' group of the aldehyde are aligned in a "zig zag" pattern in the plane of the paper (or screen), and the disposition of the formed stereocenters is deemed syn or anti, depending if they are on the same or opposite sides of the main chain.

Older papers use the erythro/threo nomenclature familiar from carbohydrate chemistry.

Read more about this topic:  Aldol Reaction

Other articles related to "stereoselectivity":

Kumada Coupling - Selectivity - Stereoselectivity
... Conversely, a Kumada coupling using vinylic Grignard reagents proceeds without stereospecificity to form a mixture of cis- and trans-alkenes ... The degree of isomerization is dependent on a variety of factors including reagent ratios and the identity of the halide group ...
Meerwein–Ponndorf–Verley Reduction - Stereoselectivity
... One method of achieving the asymmetric MPV reduction is with the use of chiral hydride donating alcohols ... The use of chiral alcohol (R)-(+)-sec-o-bromophen-ethyl alcohol gave 82%ee (percent enantiomeric excess) in the reduction of 2-chloroacetophenone ...