Catalytic Asymmetric Reductive Acyl Cross-Coupling: Synthesis of Enantioenriched Acyclic α,α-Disubstituted Ketones

被引：320

作者：

Cherney, Alan H. ^{[1
]}

Kadunce, Nathaniel T. ^{[1
]}

Reisman, Sarah E. ^{[1
]}

机构：

[1] CALTECH, Div Chem & Chem Engn, Warren & Katharine Schlinger Lab Chem & Chem Engn, Pasadena, CA 91125 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 20期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE ALPHA-ARYLATION; UNACTIVATED ALKYL-HALIDES; CARBON BOND FORMATION; ALLYLIC ALKYLATION; ARYL HALIDES; CONJUGATE ADDITION; ORGANIC HALIDES; ACID-CHLORIDES; PALLADIUM; COMPLEXES;

D O I：

10.1021/ja402922w

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first enantioselective Ni-catalyzed reductive acyl cross-coupling has been developed. Treatment of acid chlorides and racemic secondary benzyl chlorides with a Ni-II/bis(oxazoline) catalyst in the presence of Mn-0 as a stoichiometric reductant generates acyclic alpha,alpha-disubstituted ketones in good yields and high enantioselectivity without requiring stoichiometric chiral auxiliaries or pregeneration of organometallic reagents. The mild, base-free reaction conditions are tolerant of a variety of functional groups on both coupling partners.

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页码：7442 / 7445

页数：4

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