Chiral dienolate chemistry in remote asymmetric induction: The allylation/Cope rearrangement sequence leading to γ-chiral α,β-unsaturated acid derivatives

Katsuhiko Tomooka; Atsushi Nagasawa; Shih Yi Wei; Takeshi Nakai

doi:10.1016/S0040-4039(96)02077-1

Chiral dienolate chemistry in remote asymmetric induction: The allylation/Cope rearrangement sequence leading to γ-chiral α,β-unsaturated acid derivatives

Katsuhiko Tomooka, Atsushi Nagasawa, Shih Yi Wei, Takeshi Nakai

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

30 Citations (Scopus)

Abstract

The allylation of the dienolate derived from the chiral α, β- or β,γ-unsaturated imide followed by the Cope rearrangement is shown to effect the net remote asymmetric induction to create a new chirality of either configuration at the γ-position in high % de. The utility of this approach is shown in the asymmetric synthesis of the C6 side chain of zaragozic acid A. Copyright (C) 1996 Elsevier Science Ltd.

Original language	English
Pages (from-to)	8895-8898
Number of pages	4
Journal	Tetrahedron Letters
Volume	37
Issue number	49
DOIs	https://doi.org/10.1016/S0040-4039(96)02077-1
Publication status	Published - Dec 2 1996
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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T2 - The allylation/Cope rearrangement sequence leading to γ-chiral α,β-unsaturated acid derivatives

AU - Tomooka, Katsuhiko

AU - Nagasawa, Atsushi

AU - Wei, Shih Yi

AU - Nakai, Takeshi

PY - 1996/12/2

Y1 - 1996/12/2

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AB - The allylation of the dienolate derived from the chiral α, β- or β,γ-unsaturated imide followed by the Cope rearrangement is shown to effect the net remote asymmetric induction to create a new chirality of either configuration at the γ-position in high % de. The utility of this approach is shown in the asymmetric synthesis of the C6 side chain of zaragozic acid A. Copyright (C) 1996 Elsevier Science Ltd.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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ER -

Chiral dienolate chemistry in remote asymmetric induction: The allylation/Cope rearrangement sequence leading to γ-chiral α,β-unsaturated acid derivatives

Abstract

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