Olefinic stereoselection in the [2,3]-Wittig rearrangement of α,β- disubstituted allylic ethers forming trisubstituted olefins

Katsuhiko Tomooka; Tatsuya Igarashi; Naoyuki Kishi; Takeshi Nakai

doi:10.1016/S0040-4039(99)01195-8

Olefinic stereoselection in the [2,3]-Wittig rearrangement of α,β- disubstituted allylic ethers forming trisubstituted olefins

Katsuhiko Tomooka, Tatsuya Igarashi, Naoyuki Kishi, Takeshi Nakai

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

6 Citations (Scopus)

Abstract

The E/Z-selectivities in the [2,3]-Wittig rearrangements of secondary β-(methyl or silyl)allylic ethers are shown to depend critically on the nature of groups on the carbanion terminus, thereby permitting elucidation of the structural requirements for attaining high Z-selectivity.

Original language	English
Pages (from-to)	6257-6260
Number of pages	4
Journal	Tetrahedron Letters
Volume	40
Issue number	34
DOIs	https://doi.org/10.1016/S0040-4039(99)01195-8
Publication status	Published - Aug 20 1999
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/S0040-4039(99)01195-8

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abstract = "The E/Z-selectivities in the [2,3]-Wittig rearrangements of secondary β-(methyl or silyl)allylic ethers are shown to depend critically on the nature of groups on the carbanion terminus, thereby permitting elucidation of the structural requirements for attaining high Z-selectivity.",

author = "Katsuhiko Tomooka and Tatsuya Igarashi and Naoyuki Kishi and Takeshi Nakai",

year = "1999",

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AU - Tomooka, Katsuhiko

AU - Igarashi, Tatsuya

AU - Kishi, Naoyuki

AU - Nakai, Takeshi

PY - 1999/8/20

Y1 - 1999/8/20

N2 - The E/Z-selectivities in the [2,3]-Wittig rearrangements of secondary β-(methyl or silyl)allylic ethers are shown to depend critically on the nature of groups on the carbanion terminus, thereby permitting elucidation of the structural requirements for attaining high Z-selectivity.

AB - The E/Z-selectivities in the [2,3]-Wittig rearrangements of secondary β-(methyl or silyl)allylic ethers are shown to depend critically on the nature of groups on the carbanion terminus, thereby permitting elucidation of the structural requirements for attaining high Z-selectivity.

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U2 - 10.1016/S0040-4039(99)01195-8

DO - 10.1016/S0040-4039(99)01195-8

M3 - Article

AN - SCOPUS:0033588315

SN - 0040-4039

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 34

ER -

Olefinic stereoselection in the [2,3]-Wittig rearrangement of α,β- disubstituted allylic ethers forming trisubstituted olefins

Abstract

All Science Journal Classification (ASJC) codes

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