Catalytic Enantioselective Synthesis of Amino Skipped Diynes

被引：51

作者：

Paioti, Paulo H. S. ^{[1
]}

Abboud, Khalil A. ^{[2
]}

Aponick, Aaron ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Univ Florida, Dept Chem, Ctr Xray Crystallog, Gainesville, FL 32611 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 07期

基金：

美国国家科学基金会;

关键词：

ASYMMETRIC-SYNTHESIS; CONJUGATE ADDITION; NATURAL-PRODUCTS; COPPER; PROPARGYLAMINES; HYDROAMINATION; IMINES; INDOLE; ISOMERIZATION; BIOSYNTHESIS;

D O I：

10.1021/jacs.5b13387

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The Cu-catalyzed synthesis of nonracemic 3-amino skipped diynes via an enantiodetermining C-C bond formation is described using StackPhos as ligand. Despite challenging issues of reactivity and stereo selectivity inherent to these chiral skipped diynes, the reaction tolerates an extremely broad substrate scope with respect to all components and provides the title compounds in excellent enantiomeric excess. The alkyne moieties are demonstrated here to be useful synthetic handles, and 3-amino skipped diynes are convenient building blocks for enantioselective synthesis.

引用

页码：2150 / 2153

页数：4

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