Enantioselective α-Arylation of Aldehydes via the Productive Merger of lodonium Salts and Organocatalysis

被引：260

作者：

Allen, Anna E. ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 12期

基金：

加拿大自然科学与工程研究理事会;

关键词：

SILYL ENOL ETHERS; DIARYLIODONIUM SALTS; CROSS-COUPLINGS; REGIOCONTROLLED SYNTHESIS; SELECTIVE ARYLATION; IODONIUM SALTS; PALLADIUM; PHENYLATION; TRIFLUOROMETHYLATION; KETONES;

D O I：

10.1021/ja2008906

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective alpha-arylation of aldehydes has been accomplished using diaiyliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.

引用

页码：4260 / 4263

页数：4

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