Enantioselective Direct α-Annination of Aldehydes via a Photoredox Mechanism: A Strategy for Asymmetric Amine Fragment Coupling

被引：210

作者：

Cecere, Giuseppe ^{[1
]}

Koenig, Christian M. ^{[1
]}

Alleva, Jennifer L. ^{[1
]}

MacMillan, David W. C. ^{[1
]}

机构：

[1] Princeton Univ, Merck Ctr Catalysis, Princeton, NJ 08544 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2013年 / 135卷 / 31期

关键词：

MULTIPLE N-METHYLATION; TRANSFER HYDROAMINATION; AMIDYL RADICALS; CYCLIZATION; GENERATION; AMINATION; REACTIVITY; CATALYSIS; PEPTIDES; KINETICS;

D O I：

10.1021/ja406181e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct, asymmetric alpha-amination of aldehydes has been accomplished via a combination of photoredox and organocatalysis. Photon-generated N-centered radicals undergo enantioselective alpha-addition to catalytically formed chiral enamines to directly produce stable alpha-amino aldehyde adducts bearing synthetically useful amine substitution patterns. Incorporation of a photolabile group on the amine precursor obviates the need to employ a photoredox catalyst in this transformation. Importantly, this photoinduced transformation allows direct and enantioselective access to alpha-amino aldehyde products that do not require postreaction manipulation.

引用

页码：11521 / 11524

页数：4

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