Synthesis of chiral α-hydroxy acids via palladium-catalyzed C(sp3)-H alkylation of lactic acid

被引：22
|
作者：
Chen, Kai [1 ,2 ]
Li, Xin [1 ]
Zhang, Shuo-Qing [1 ]
Shi, Bing-Feng [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
[2] CALTECH, Div Chem & Chem Engn, Pasadena, CA 91125 USA
来源：
CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 09期
关键词：
C-H BONDS; UNACTIVATED C(SP(3))-H; STEREOSELECTIVE-SYNTHESIS; DIRECTING GROUPS; AMINO-ACIDS; CROSS-COUPLINGS; ARYLATION; BIOMASS; SP(2); FUNCTIONALIZATION;
D O I：
10.1039/c5cc07879b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Herein we report a Pd-catalyzed alkylation of lactic acid with the assistance of 8-aminoquinoline auxiliary. A wide range of alkyl iodides bearing beta-hydrogen atoms are compatible with the reaction conditions, providing a practical and straightforward alternative to access chiral alpha-hydroxy acids (AHAs). The new reactions have been applied for the synthesis of isotope-labeled AHAs and a sugar-containing complex AHA.
引用
收藏
页码：1915 / 1918
页数：4
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