Direct Enantioselective Conjugate Addition of Carboxylic Acids with Chiral Lithium Amides as Traceless Auxiliaries

被引：38
|
作者：
Lu, Ping [1 ]
Jackson, Jeffrey J. [1 ]
Eickhoff, John A. [1 ]
Zakarian, Armen [1 ]
机构：
[1] Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 02期
关键词：
MICHAEL REACTIONS; ARYLACETIC ACIDS; ESTER; ALKYLATION; PSEUDOEPHEDRINE; REAGENT;
D O I：
10.1021/ja512213c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Michael addition is a premier synthetic method for carbon-carbon and carbon-heteroatom bond formation. Using chiral dilithium amides as traceless auxiliaries, we report the direct enantioselective Michael addition of carboxylic acids. A free carboxyl group in the product provides versatility for further functionalization, and the chiral reagent can be readily recovered by extraction with aqueous acid. The method has been applied in the enantioselective total synthesis of the purported structure of pulveraven B.
引用
收藏
页码：656 / 659
页数：4
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