Palladium(II)-Catalyzed Enantioselective C(sp3)-H Activation Using a Chiral Hydroxamic Acid Ligand

被引：208
|
作者：
Xiao, Kai-Jiong [1 ]
Lin, David W. [1 ]
Miura, Motofumi [1 ]
Zhu, Ru-Yi [1 ]
Gong, Wei [1 ]
Wasa, Masayuki [1 ]
Yu, Jin-Quan [1 ]
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 22期
基金：
美国国家卫生研究院;
关键词：
H BOND ACTIVATION; N-METHOXYBENZAMIDES; ASYMMETRIC-SYNTHESIS; FUSED INDOLINES; CONSTRUCTION; FUNCTIONALIZATION; ARYLATION; CYCLOBUTANES; OXIDATION; EFFICIENT;
D O I：
10.1021/ja504196j
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An enantioselective method for Pd(II)-catalyzed cross-coupling of methylene beta-C(sp(3))-H bonds in cyclobutanecarboxylic acid derivatives with arylboron reagents is described. High yields and enantioselectivities were achieved through the development of chiral mono-N-protected alpha-amino-O-methylhydroxamic acid (MPAHA) ligands, which form a chiral complex with the Pd(II) center. This reaction provides an alternative approach to the enantioselective synthesis of cyclobutanecarboxylates containing alpha-chiral quaternary stereocenters. This new class of chiral catalysts also show promises for enantioselective beta-C(sp(3))-H activation of acyclic amides.
引用
收藏
页码：8138 / 8142
页数：5
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