Direct catalytic asymmetric addition of allylic cyanides to aldehydes for expeditious access to enantioenriched unsaturated δ-valerolactones

Yasunari Otsuka; Hisashi Takada; Shigeo Yasuda; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1002/asia.201201021

Direct catalytic asymmetric addition of allylic cyanides to aldehydes for expeditious access to enantioenriched unsaturated δ-valerolactones

Yasunari Otsuka, Hisashi Takada, Shigeo Yasuda, Naoya Kumagai, Masakatsu Shibasaki

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

23 Citations (Scopus)

Abstract

A direct catalytic asymmetric γ-addition of allyl cyanide to aldehydes promoted by soft Lewis acid/hard Brønsted base cooperative catalysis is described. The resulting homoallylic alcohols bearing a Z-configured α,β-unsaturated nitrile allow rapid access to enantioenriched δ-valerolactones.

Original language	English
Pages (from-to)	354-358
Number of pages	5
Journal	Chemistry - An Asian Journal
Volume	8
Issue number	2
DOIs	https://doi.org/10.1002/asia.201201021
Publication status	Published - 2013 Feb
Externally published	Yes

Keywords

allyl cyanides
asymmetric catalysis
atom economy
fostriecin
homogeneous catalysis

ASJC Scopus subject areas

Biochemistry
Organic Chemistry

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10.1002/asia.201201021

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abstract = "A direct catalytic asymmetric γ-addition of allyl cyanide to aldehydes promoted by soft Lewis acid/hard Br{\o}nsted base cooperative catalysis is described. The resulting homoallylic alcohols bearing a Z-configured α,β-unsaturated nitrile allow rapid access to enantioenriched δ-valerolactones.",

keywords = "allyl cyanides, asymmetric catalysis, atom economy, fostriecin, homogeneous catalysis",

author = "Yasunari Otsuka and Hisashi Takada and Shigeo Yasuda and Naoya Kumagai and Masakatsu Shibasaki",

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journal = "Chemistry - An Asian Journal",

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T1 - Direct catalytic asymmetric addition of allylic cyanides to aldehydes for expeditious access to enantioenriched unsaturated δ-valerolactones

AU - Otsuka, Yasunari

AU - Takada, Hisashi

AU - Yasuda, Shigeo

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2013/2

Y1 - 2013/2

N2 - A direct catalytic asymmetric γ-addition of allyl cyanide to aldehydes promoted by soft Lewis acid/hard Brønsted base cooperative catalysis is described. The resulting homoallylic alcohols bearing a Z-configured α,β-unsaturated nitrile allow rapid access to enantioenriched δ-valerolactones.

AB - A direct catalytic asymmetric γ-addition of allyl cyanide to aldehydes promoted by soft Lewis acid/hard Brønsted base cooperative catalysis is described. The resulting homoallylic alcohols bearing a Z-configured α,β-unsaturated nitrile allow rapid access to enantioenriched δ-valerolactones.

KW - allyl cyanides

KW - asymmetric catalysis

KW - atom economy

KW - fostriecin

KW - homogeneous catalysis

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JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

IS - 2

ER -

Direct catalytic asymmetric addition of allylic cyanides to aldehydes for expeditious access to enantioenriched unsaturated δ-valerolactones

Abstract

Keywords

ASJC Scopus subject areas

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