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

被引：259
|
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
收藏
页码：4260 / 4263
页数：4
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