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Trans stereoselectivity in the reaction of (4-carboxybutylidene)triphenylphosphorane with aromatic aldehydes

✍ Scribed by Bruce E. Maryanoff; Barbara A. Duhl-Emswiler

Publisher: Elsevier Science
Year: 1981
Tongue: French
Weight: 275 KB
Volume: 22
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(01)82099-2

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✦ Synopsis

Aromatic aldehydes react with J, to give predominantly trans 6-aryl-5-hexenoic acids, under special conditions. A systematic study of the reaction of k with aldehydes, in a preliminary attempt to define the cause and scope of the trans stereoselectivity, is reported.

The Wittig reaction can be an effective method for stereoselective synthesis of carboncarbon double bonds.

1 Aldehydes react with lithium-salt-free, non-stabilized (or "reactive") phosphonium ylides to produce predominantly cis olefins, and with stabilized ylides to produce predominantly trans olefins.' Generally, non-stabilized ylides will not afford high trans stereoselectivity directly in their reaction with aldehydes, even in the midst of lithium salts and non-polar solvents.

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