Direct organocatalytic enantioselective α-aminomethylation of ketones

被引：74

作者：

Ibrahem, I ^{[1
]}

Zou, WB ^{[1
]}

Casas, J ^{[1
]}

Sundén, H ^{[1
]}

Córdova, A ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2006年 / 62卷 / 2-3期

关键词：

asymmetric catalysis; proline derivatives; ketones; alpha-aminomethylation; classical Mannich reaction;

D O I：

10.1016/j.tet.2005.08.113

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The scope and limitations of the direct organocatalytic asymmetric alpha-aminomethylation of ketones are disclosed. The proline-catalyzed classical Mannich reactions between unmodified ketones, aqueous formaldehyde and aromatic amines furnished the desired Mannich bases in high yield with up to > 99% cc. Moreover, methyl alkyl ketones were regioselectively alpha-aminomethylated at the methylene carbon affording the corresponding Mannich products with up to > 99% cc. In addition, the proline-catalyzed one-pot three-component reaction between p-anisidine, aqueous formaldehyde and 4,4-dimethyl-2-cycloxehen-1-one furnished the corresponding bicyclic aza-Diels-Alder adduct with > 99% ee. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：357 / 364

页数：8

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