Wittig Rearrangement of α-(Propargyloxy)alkyllithiums: Periselectivity and Steric Course at the Lithium-Bearing Terminus

Katsuhiko Tomooka; Nobuyuki Komine; Takeshi Nakai

doi:10.1055/s-1997-1551

Wittig Rearrangement of α-(Propargyloxy)alkyllithiums: Periselectivity and Steric Course at the Lithium-Bearing Terminus

Katsuhiko Tomooka, Nobuyuki Komine, Takeshi Nakai

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

13 Citations (Scopus)

Abstract

The [2,3]-Wittig rearrangement of an enantiomerically defined α-propargyloxy stannane with butyllithium is shown to proceed with complete inversion of configuration at the Li-bearing terminus. The periselectivity ([2,3]- vs. [1,2]-) of the rearrangement depends markedly upon the nature of substituents on the acetylenic group.

Original language	English
Pages (from-to)	1045-1046
Number of pages	2
Journal	Synlett
Volume	1997
Issue number	9
DOIs	https://doi.org/10.1055/s-1997-1551
Publication status	Published - Jan 1 1997
Externally published	Yes

All Science Journal Classification (ASJC) codes

Organic Chemistry

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10.1055/s-1997-1551

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abstract = "The [2,3]-Wittig rearrangement of an enantiomerically defined α-propargyloxy stannane with butyllithium is shown to proceed with complete inversion of configuration at the Li-bearing terminus. The periselectivity ([2,3]- vs. [1,2]-) of the rearrangement depends markedly upon the nature of substituents on the acetylenic group.",

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AU - Nakai, Takeshi

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AB - The [2,3]-Wittig rearrangement of an enantiomerically defined α-propargyloxy stannane with butyllithium is shown to proceed with complete inversion of configuration at the Li-bearing terminus. The periselectivity ([2,3]- vs. [1,2]-) of the rearrangement depends markedly upon the nature of substituents on the acetylenic group.

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Wittig Rearrangement of α-(Propargyloxy)alkyllithiums: Periselectivity and Steric Course at the Lithium-Bearing Terminus

Abstract

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