Sequential Reductive Amination-Hydrogenolysis: A One-Pot Synthesis of Challenging Chiral Primary Amines

被引：39

作者：

Nugent, Thomas C. ^{[1
]}

Negru, Daniela E. ^{[1
]}

El-Shazly, Mohamed ^{[1
]}

Hu, Dan ^{[1
]}

Sadiq, Abdul ^{[1
]}

Bibi, Ahtaram ^{[1
]}

Umar, M. Naveed ^{[1
]}

机构：

[1] Jacobs Univ Bremen, Dept Chem, Sch Sci & Engn, D-28759 Bremen, Germany

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2011年 / 353卷 / 11-12期

关键词：

asymmetric reductive amination; chiral amines; hydrogenolysis; primary amine synthesis; CATALYZED ASYMMETRIC HYDROGENATION; HIGHLY ENANTIOSELECTIVE HYDROGENATION; PHOSPHORAMIDITE LIGANDS; ACID; RESOLUTION; ENAMIDES; ALLYLATION; IMINES; ALKYL;

D O I：

10.1002/adsc.201100250

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Difficult-to-access chiral primary amines were formed in good to high yield and ee using a rare example of a one-pot synthesis from prochiral ketones (sequential reductive amination-hydrogenloysis). As a highlight we also demonstrate a one-pot reductive amination-hydrogenolysis-reductive amination (five reactions) of ortho-methoxyacetophenone resulting in the chiral diamine 1-(2-methoxy-phenyl)ethyl-(2-pyridylmethyl)-amine (4) (58% overall yield, >99% ee), a new organocatalyst for aqueous enantioselective aldol reactions.

引用

页码：2085 / 2092

页数：8

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