Stereochemistry and mechanism of vinyl-migrating [1,2]-Wittig rearrangement of α-lithioalkyl vinyl ethers

Katsuhiko Tomooka; Tadashi Inoue; Takeshi Nakai

doi:10.1246/cl.2000.418

Stereochemistry and mechanism of vinyl-migrating [1,2]-Wittig rearrangement of α-lithioalkyl vinyl ethers

Katsuhiko Tomooka, Tadashi Inoue, Takeshi Nakai

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

14 Citations (Scopus)

Abstract

Enantiomerically defined α-stannylalkyl or α-methylbenzyl vinyl ethers, when treated with butyllithium, are shown to undergo the 1,2-vinyl migration to afford the allylic alcohols in almost racemic form in low or high yield, respectively, thereby proposing the radical cleavage-recombination pathway.

Original language	English
Pages (from-to)	418-419
Number of pages	2
Journal	Chemistry Letters
Issue number	4
DOIs	https://doi.org/10.1246/cl.2000.418
Publication status	Published - 2000
Externally published	Yes

All Science Journal Classification (ASJC) codes

Chemistry(all)

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10.1246/cl.2000.418

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title = "Stereochemistry and mechanism of vinyl-migrating [1,2]-Wittig rearrangement of α-lithioalkyl vinyl ethers",

abstract = "Enantiomerically defined α-stannylalkyl or α-methylbenzyl vinyl ethers, when treated with butyllithium, are shown to undergo the 1,2-vinyl migration to afford the allylic alcohols in almost racemic form in low or high yield, respectively, thereby proposing the radical cleavage-recombination pathway.",

author = "Katsuhiko Tomooka and Tadashi Inoue and Takeshi Nakai",

year = "2000",

doi = "10.1246/cl.2000.418",

language = "English",

pages = "418--419",

journal = "Chemistry Letters",

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publisher = "The Chemical Society of Japan",

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AU - Tomooka, Katsuhiko

AU - Inoue, Tadashi

AU - Nakai, Takeshi

PY - 2000

Y1 - 2000

N2 - Enantiomerically defined α-stannylalkyl or α-methylbenzyl vinyl ethers, when treated with butyllithium, are shown to undergo the 1,2-vinyl migration to afford the allylic alcohols in almost racemic form in low or high yield, respectively, thereby proposing the radical cleavage-recombination pathway.

AB - Enantiomerically defined α-stannylalkyl or α-methylbenzyl vinyl ethers, when treated with butyllithium, are shown to undergo the 1,2-vinyl migration to afford the allylic alcohols in almost racemic form in low or high yield, respectively, thereby proposing the radical cleavage-recombination pathway.

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JF - Chemistry Letters

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ER -

Stereochemistry and mechanism of vinyl-migrating [1,2]-Wittig rearrangement of α-lithioalkyl vinyl ethers

Abstract

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