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

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)]

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https://libra.unine.ch/handle/123456789/21467

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journal article

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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

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