Direct catalytic asymmetric addition of allylic cyanides to ketoimines

Ryo Yazaki; Tatsuya Nitabaru; Naoya Kumagai; Masakatsu Shibasaki

doi:10.1021/ja806572b

Direct catalytic asymmetric addition of allylic cyanides to ketoimines

Ryo Yazaki, Tatsuya Nitabaru, Naoya Kumagai, Masakatsu Shibasaki

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

87 Citations (Scopus)

Abstract

Direct catalytic asymmetric addition of allylic cyanides to N-diphenylphosphinoyl ketoimines with a bimetallic catalytic system comprising Ph-BPE/[Cu(CH₃CN)₄]ClO₄/LiOAr is described. Intermediary α-adducts readily isomerized to afford synthetically useful α,β-unsaturated nitriles bearing an optically active tetrasubstituted carbon. Applicability to aromatic, heteroaromatic, and aliphatic ketoimines exemplifies wide substrate generality. Transformation of the product into densely functionalized material showcases the utility of the present protocol.

Original language	English
Pages (from-to)	14477-14479
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	130
Issue number	44
DOIs	https://doi.org/10.1021/ja806572b
Publication status	Published - Nov 5 2008
Externally published	Yes

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja806572b

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title = "Direct catalytic asymmetric addition of allylic cyanides to ketoimines",

abstract = "Direct catalytic asymmetric addition of allylic cyanides to N-diphenylphosphinoyl ketoimines with a bimetallic catalytic system comprising Ph-BPE/[Cu(CH3CN)4]ClO4/LiOAr is described. Intermediary α-adducts readily isomerized to afford synthetically useful α,β-unsaturated nitriles bearing an optically active tetrasubstituted carbon. Applicability to aromatic, heteroaromatic, and aliphatic ketoimines exemplifies wide substrate generality. Transformation of the product into densely functionalized material showcases the utility of the present protocol.",

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

year = "2008",

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doi = "10.1021/ja806572b",

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T1 - Direct catalytic asymmetric addition of allylic cyanides to ketoimines

AU - Yazaki, Ryo

AU - Nitabaru, Tatsuya

AU - Kumagai, Naoya

AU - Shibasaki, Masakatsu

PY - 2008/11/5

Y1 - 2008/11/5

N2 - Direct catalytic asymmetric addition of allylic cyanides to N-diphenylphosphinoyl ketoimines with a bimetallic catalytic system comprising Ph-BPE/[Cu(CH3CN)4]ClO4/LiOAr is described. Intermediary α-adducts readily isomerized to afford synthetically useful α,β-unsaturated nitriles bearing an optically active tetrasubstituted carbon. Applicability to aromatic, heteroaromatic, and aliphatic ketoimines exemplifies wide substrate generality. Transformation of the product into densely functionalized material showcases the utility of the present protocol.

AB - Direct catalytic asymmetric addition of allylic cyanides to N-diphenylphosphinoyl ketoimines with a bimetallic catalytic system comprising Ph-BPE/[Cu(CH3CN)4]ClO4/LiOAr is described. Intermediary α-adducts readily isomerized to afford synthetically useful α,β-unsaturated nitriles bearing an optically active tetrasubstituted carbon. Applicability to aromatic, heteroaromatic, and aliphatic ketoimines exemplifies wide substrate generality. Transformation of the product into densely functionalized material showcases the utility of the present protocol.

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DO - 10.1021/ja806572b

M3 - Article

C2 - 18844357

AN - SCOPUS:55549141880

SN - 0002-7863

VL - 130

SP - 14477

EP - 14479

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 44

ER -

Direct catalytic asymmetric addition of allylic cyanides to ketoimines

Abstract

All Science Journal Classification (ASJC) codes

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