Expedient synthesis of chiral 1,2- and 1,4-diamines: Protecting group dependent regioselectivity in direct organocatalytic asymmetric Mannich reactions

被引：127

作者：

Chowdari, Naidu S.

Ahmad, Moballigh

Albertshofer, Klaus

Tanaka, Fujie

Barbas, Carlos F., III

机构：

[1] Skaggs Inst Chem Biol, La Jolla, CA 92037 USA

[2] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

[3] Scripps Res Inst, Dept Mol Biol, La Jolla, CA 92037 USA

来源：

ORGANIC LETTERS | 2006年 / 8卷 / 13期

关键词：

D O I：

10.1021/ol060980d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Organocatalytic asymmetric Mannich reaction of protected amino ketones with imines in the presence of an L-proline-derived tetrazole catalyst afforded diamines with excellent yields and enantioselectivities of up to 99%. The amino ketone protecting group controlled the regioselectivity of the reaction providing access to chiral 1,2-diamines from azido ketones and 1,4-diamines from phthalimido ketones.

引用

页码：2839 / 2842

页数：4

共 74 条

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