Acyclic chiral amines and amino acids as inexpensive and readily tunable catalysts for the direct asymmetric three-component Mannich reaction

被引：149

作者：

Ibrahem, I ^{[1
]}

Zou, WB ^{[1
]}

Engqvist, M ^{[1
]}

Xu, YM ^{[1
]}

Córdova, A ^{[1
]}

机构：

[1] Univ Stockholm, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2005年 / 11卷 / 23期

关键词：

acyclic; amino acids; asymmetric catalysis; chiral amines; Mannich reaction;

D O I：

10.1002/chem.200500746

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The direct three-component asymmetric Mannich reaction catalyzed by acyclic chiral amines or amino acids is presented. Simple acyclic chiral amines and amino acids-such as alanine-tetrazole (9), alanine, valine, and serine-catalyzed the three-component asymmetric Mannich reactions between unmodified ketones, p-anisidine, and aldehydes with high chemo- and stereoselectivity, furnishing the corresponding Mannich bases with up to > 99 % ee. This study demonstrates that the whole range of amino acids in nature, as well as nonproteogenic amino acid derivatives, can be considered in the design and tuning of novel, inexpensive organocatalysts for the direct asymmetric Mannich reaction.

引用

页码：7024 / 7029

页数：6

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