Copper-Catalyzed Conjugate Additions of Alkylboranes to Imidazolyl α,β-Unsaturated Ketones: Formal Reductive Conjugate Addition of Terminal Alkenes

被引：35

作者：

Ohmiya, Hirohisa ^{[1
]}

Yoshida, Mika ^{[1
]}

Sawamura, Masaya ^{[1
]}

机构：

[1] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan

来源：

ORGANIC LETTERS | 2011年 / 13卷 / 03期

关键词：

N-HETEROCYCLIC CARBENES; CARBONYL-COMPOUNDS; ARYLBORONIC ACIDS; GRIGNARD-REAGENTS; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC 1,4-ADDITION; DIORGANOZINC REAGENTS; DIASTEREOSELECTIVE SYNTHESIS; SUBSTITUTION-REACTIONS; TRISUBSTITUTED ENONES;

D O I：

10.1021/ol102819k

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conjugate addition of alkylboron compounds (allryl-9-BBN) to imidazol-2-yl alpha,beta-unsaturated ketones proceeded in the presence of a catalytic amount (10 mol %) of CuCl, 1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene (IMes), and t-BuOK. The alkylboranes are available through alkene hydroboration, and thus the overall process represents a reductive conjugate addition of alkenes to enone derivatives. A variety of functional groups are tolerated in both the alkenes and the alpha,beta-unsaturated ketones. The 2-acylimidazole moiety can easily be converted into the corresponding carboxylic acid, ester, and amide derivatives.

引用

页码：482 / 485

页数：4

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