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

被引：219

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

页码：8138 / 8142

页数：5

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