Organocatalytic asymmetric Michael addition of 2,2-dimethyl-1,3-dioxan-5-one to nitro alkenes employing proline-based catalysts

被引：55

作者：

Enders, Dieter ^{[1
]}

Chow, Sharon ^{[1
]}

机构：

[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2006年 / 2006卷 / 20期

关键词：

asymmetric synthesis; Michael addition; organocatalysis; dioxanone; nitro alkenes; proline-based catalysts;

D O I：

10.1002/ejoc.200600464

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The organocatalytic asymmetric Michael addition of 2,2-dimethyl-1,3-dioxiin-5-one (1) was performed with various nitro alkenes 2 using a number of proline-based catalysts (AM) affording polyfunctional nitro ketones 3. Reverse diastereoselectivity was observed with the diphenylprolinol catalyst J, and the best diastereo- and enantiomeric excesses were achieved with the sulfonamide catalyst M (de = 84-98%, ee = 81-86%). ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006).

引用

页码：4578 / 4584

页数：7

共 61 条

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