Direct catalytic asymmetric addition of allyl cyanide to ketones

Ryo Yazaki; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/ja900001u

Direct catalytic asymmetric addition of allyl cyanide to ketones

Ryo Yazaki, Naoya Kumagai, Masakatsu Shibasaki

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

68 Citations (Scopus)

Abstract

A direct catalytic asymmetric addition of allyl cyanide to ketones with a bimetallic catalytic system comprising (R,R)-Ph-BPE/[Cu(CH₃CN) ₄]ClO₄/LiOAr is described. Exclusive γ-addition of allyl cyanide was observed, affording optically enriched tertiary alcohols bearing Z-configured α,ß-unsaturated nitriles. The reaction proceeded under proton-transfer conditions, utilizing soft Lewis acid/hard Brønsted base bifunctional catalysis. The applicability of the reaction to aromatic, heteroaromatic, and aliphatic ketones demonstrates its wide substrate generality.

Original language	English
Pages (from-to)	3195-3197
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	131
Issue number	9
DOIs	https://doi.org/10.1021/ja900001u
Publication status	Published - Mar 11 2009
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja900001u

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abstract = "A direct catalytic asymmetric addition of allyl cyanide to ketones with a bimetallic catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]ClO4/LiOAr is described. Exclusive γ-addition of allyl cyanide was observed, affording optically enriched tertiary alcohols bearing Z-configured α,{\ss}-unsaturated nitriles. The reaction proceeded under proton-transfer conditions, utilizing soft Lewis acid/hard Br{\o}nsted base bifunctional catalysis. The applicability of the reaction to aromatic, heteroaromatic, and aliphatic ketones demonstrates its wide substrate generality.",

author = "Ryo Yazaki and Naoya Kumagai and Masakatsu Shibasaki",

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doi = "10.1021/ja900001u",

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T1 - Direct catalytic asymmetric addition of allyl cyanide to ketones

AU - Yazaki, Ryo

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2009/3/11

Y1 - 2009/3/11

N2 - A direct catalytic asymmetric addition of allyl cyanide to ketones with a bimetallic catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]ClO4/LiOAr is described. Exclusive γ-addition of allyl cyanide was observed, affording optically enriched tertiary alcohols bearing Z-configured α,ß-unsaturated nitriles. The reaction proceeded under proton-transfer conditions, utilizing soft Lewis acid/hard Brønsted base bifunctional catalysis. The applicability of the reaction to aromatic, heteroaromatic, and aliphatic ketones demonstrates its wide substrate generality.

AB - A direct catalytic asymmetric addition of allyl cyanide to ketones with a bimetallic catalytic system comprising (R,R)-Ph-BPE/[Cu(CH3CN) 4]ClO4/LiOAr is described. Exclusive γ-addition of allyl cyanide was observed, affording optically enriched tertiary alcohols bearing Z-configured α,ß-unsaturated nitriles. The reaction proceeded under proton-transfer conditions, utilizing soft Lewis acid/hard Brønsted base bifunctional catalysis. The applicability of the reaction to aromatic, heteroaromatic, and aliphatic ketones demonstrates its wide substrate generality.

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JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 9

ER -

Direct catalytic asymmetric addition of allyl cyanide to ketones

Abstract

All Science Journal Classification (ASJC) codes

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