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Rac-(2R*,3R*)-S-Ethyl-4-Chloro-3-Hydroxy-2-Phenylbuthanethioate and Rac-(2R*,3R*)-S-Ethyl-2-Phenyl-3-(tosyloxy)buthanethioate: Dichotomy of the Stereoselectivity of the Mukaiyama Reaction

Auteur(s)
Vallat, Olivier
Date de parution
2010
In
J. Chem. Crystallogr.
Vol.
1
No
40
De la page
10
A la page
14
Mots-clés
Résumé
The compds., rac-(2R*,3R*)-S-ethyl-4-chloro-3-hydroxy-2-phenylbuthanethioate (I) and rac-(2R*,3R*)-S-ethyl-3-hydroxy-2-phenylbuthanethioate (II), were prepd. by the Mukaiyama crossed aldol reaction between the silyl enol ether of S-Et 2-phenylethanethioate and simple aldehydes, like 2-chloroacetaldehyde (for I) and acetaldehyde (for II). The stereoselectivity of the Mukaiyama aldol reaction has switched from a syn selective process for the reaction using 2-chloroacetaldehyde to an anti selective process for the reaction with acetaldehyde. [on SciFinder(R)]
URI
Type de publication
Resource Types::text::journal::journal article