Stereospecific internal almylation of terminal γ,δ-epoxy acrylates

Masahiro Miyazawa; Naoki Ishibashi; Satoshi Ohnuma; Masaaki Miyashita

doi:10.1016/S0040-4039(97)00635-7

Stereospecific internal almylation of terminal γ,δ-epoxy acrylates

Masahiro Miyazawa^*, Naoki Ishibashi, Satoshi Ohnuma, Masaaki Miyashita

^*Corresponding author for this work

Department of Chemistry

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

27 Scopus citations

Abstract

The alkylation of ethyl (S)- and (R)-4,5-epoxy-2-pentenoates (11) and (12), chiral terminal γ,δ-epoxy acrylates prepared from D-mannitol, by trialkylaluminum in the presence of water occurs rcgioselectively at the γ position, i.e., at the internal position, to yield a sole product respectively with net inversion of configuration. The method provides useful chiral synthons for natural product synthesis.

Original language	English
Pages (from-to)	3419-3422
Number of pages	4
Journal	Tetrahedron Letters
Volume	38
Issue number	19
DOIs	https://doi.org/10.1016/S0040-4039(97)00635-7
State	Published - 1997/05/12

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Stereospecific internal almylation of terminal γ,δ-epoxy acrylates",

abstract = "The alkylation of ethyl (S)- and (R)-4,5-epoxy-2-pentenoates (11) and (12), chiral terminal γ,δ-epoxy acrylates prepared from D-mannitol, by trialkylaluminum in the presence of water occurs rcgioselectively at the γ position, i.e., at the internal position, to yield a sole product respectively with net inversion of configuration. The method provides useful chiral synthons for natural product synthesis.",

author = "Masahiro Miyazawa and Naoki Ishibashi and Satoshi Ohnuma and Masaaki Miyashita",

year = "1997",

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T1 - Stereospecific internal almylation of terminal γ,δ-epoxy acrylates

AU - Miyazawa, Masahiro

AU - Ishibashi, Naoki

AU - Ohnuma, Satoshi

AU - Miyashita, Masaaki

PY - 1997/5/12

Y1 - 1997/5/12

N2 - The alkylation of ethyl (S)- and (R)-4,5-epoxy-2-pentenoates (11) and (12), chiral terminal γ,δ-epoxy acrylates prepared from D-mannitol, by trialkylaluminum in the presence of water occurs rcgioselectively at the γ position, i.e., at the internal position, to yield a sole product respectively with net inversion of configuration. The method provides useful chiral synthons for natural product synthesis.

AB - The alkylation of ethyl (S)- and (R)-4,5-epoxy-2-pentenoates (11) and (12), chiral terminal γ,δ-epoxy acrylates prepared from D-mannitol, by trialkylaluminum in the presence of water occurs rcgioselectively at the γ position, i.e., at the internal position, to yield a sole product respectively with net inversion of configuration. The method provides useful chiral synthons for natural product synthesis.

UR - http://www.scopus.com/inward/record.url?scp=0030957830&partnerID=8YFLogxK

U2 - 10.1016/S0040-4039(97)00635-7

DO - 10.1016/S0040-4039(97)00635-7

M3 - 学術論文

AN - SCOPUS:0030957830

SN - 0040-4039

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SP - 3419

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 19

ER -

Stereospecific internal almylation of terminal γ,δ-epoxy acrylates

Abstract

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