Novel stereocontrolled synthesis of highly functionalized cyclobutanes by epoxide opening through a carbanion intermediate in heteroconjugate addition

Masaatsu Adachi; Eiji Yamauchi; Takema Komada; Minoru Isobe

doi:10.1055/s-0028-1088108

Novel stereocontrolled synthesis of highly functionalized cyclobutanes by epoxide opening through a carbanion intermediate in heteroconjugate addition

Masaatsu Adachi, Eiji Yamauchi, Takema Komada, Minoru Isobe

PHA - Molecular Pharmaceutical Science

Nagoya University

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

23 Citations (Scopus)

Abstract

We have demonstrated a new cyclobutane ring formation from the trans-1,2-disubstituted epoxides through intramolecular carbanion opening process. In this reaction, the nucleophilic carbanion is generated not via α-proton abstraction but via heteroconjugate addition. These studies indicate that the different configuration of each epoxide (syn and anti) do not affect its reactivity and the reaction velocity in the cyclization step, providing multifunctionalized cyclobutanes in a regio- and stereospecific manner.

Original language	English
Pages (from-to)	1157-1161
Number of pages	5
Journal	Synlett
Issue number	7
DOIs	https://doi.org/10.1055/s-0028-1088108
Publication status	Published - 2009 Apr

Keywords

Cyclization
Cyclobutanes
Epoxides
Heteroconjugate addition
Sulfonyl carbanion

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10.1055/s-0028-1088108

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abstract = "We have demonstrated a new cyclobutane ring formation from the trans-1,2-disubstituted epoxides through intramolecular carbanion opening process. In this reaction, the nucleophilic carbanion is generated not via α-proton abstraction but via heteroconjugate addition. These studies indicate that the different configuration of each epoxide (syn and anti) do not affect its reactivity and the reaction velocity in the cyclization step, providing multifunctionalized cyclobutanes in a regio- and stereospecific manner.",

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T1 - Novel stereocontrolled synthesis of highly functionalized cyclobutanes by epoxide opening through a carbanion intermediate in heteroconjugate addition

AU - Adachi, Masaatsu

AU - Yamauchi, Eiji

AU - Komada, Takema

AU - Isobe, Minoru

PY - 2009/4

Y1 - 2009/4

N2 - We have demonstrated a new cyclobutane ring formation from the trans-1,2-disubstituted epoxides through intramolecular carbanion opening process. In this reaction, the nucleophilic carbanion is generated not via α-proton abstraction but via heteroconjugate addition. These studies indicate that the different configuration of each epoxide (syn and anti) do not affect its reactivity and the reaction velocity in the cyclization step, providing multifunctionalized cyclobutanes in a regio- and stereospecific manner.

AB - We have demonstrated a new cyclobutane ring formation from the trans-1,2-disubstituted epoxides through intramolecular carbanion opening process. In this reaction, the nucleophilic carbanion is generated not via α-proton abstraction but via heteroconjugate addition. These studies indicate that the different configuration of each epoxide (syn and anti) do not affect its reactivity and the reaction velocity in the cyclization step, providing multifunctionalized cyclobutanes in a regio- and stereospecific manner.

KW - Cyclization

KW - Cyclobutanes

KW - Epoxides

KW - Heteroconjugate addition

KW - Sulfonyl carbanion

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Novel stereocontrolled synthesis of highly functionalized cyclobutanes by epoxide opening through a carbanion intermediate in heteroconjugate addition

Abstract

Keywords

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