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

Yoshio Nishimura; Takao Shiraishi; Masahiko Yamaguchi

doi:10.1016/j.tetlet.2008.03.086

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

Yoshio Nishimura, Takao Shiraishi, Masahiko Yamaguchi

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	3492-3495
Number of pages	4
Journal	Tetrahedron Letters
Volume	49
Issue number	21
DOIs	https://doi.org/10.1016/j.tetlet.2008.03.086
Publication status	Published - 2008 May 19
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.03.086

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abstract = "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.",

author = "Yoshio Nishimura and Takao Shiraishi and Masahiko Yamaguchi",

note = "Funding Information: Y.N. thanks JSPS for financial support (No. 18850004). ",

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T1 - (Z)-Selective Wittig and Corey-Chaykovsky reactions of propargyl ylides using trialkylgallium bases

AU - Nishimura, Yoshio

AU - Shiraishi, Takao

AU - Yamaguchi, Masahiko

N1 - Funding Information: Y.N. thanks JSPS for financial support (No. 18850004).

PY - 2008/5/19

Y1 - 2008/5/19

N2 - 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.

AB - 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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DO - 10.1016/j.tetlet.2008.03.086

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 21

ER -

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

Abstract

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