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(Z)-Selective Wittig and Corey–Chaykovsky reactions of propargyl ylides using trialkylgallium bases

✍ Scribed by Yoshio Nishimura; Takao Shiraishi; Masahiko Yamaguchi

Book ID: 104095241
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 118 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.03.086

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✦ Synopsis

Trialkylgalliums deprotonated propargylphosphonium salts and propargylsulfonium salts to form propargyl ylides. The resulted organogallium intermediates underwent the Wittig reaction and the Corey-Chaykovsky reaction with aldehydes giving (Z)-enynes and (Z)-epoxides predominantly. The use of an appropriate trialkylgallium is essential for the stereoselectivity.

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