Sequential Mannich-Aza-Michael Reactions for the Stereodivergent Synthesis of Highly Substituted Pyrrolidines

被引：25

作者：

Enkisch, Charlotte ^{[1
]}

Schneider, Christoph ^{[1
]}

机构：

[1] Univ Leipzig, Inst Organ Chem, D-04103 Leipzig, Germany

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 32期

关键词：

Asymmetric catalysis; Michael addition; Mannich reactions; Nitrogen heterocycles; Organocatalysis; Proline; ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; STEREOSELECTIVE COPE REARRANGEMENTS; SYN-ALDOL PRODUCTS; ASYMMETRIC-SYNTHESIS; AZOMETHINE YLIDES; FUNCTIONALIZED PYRROLIDINES; TRANS-2,5-DISUBSTITUTED PYRROLIDINES; ENANTIOSPECIFIC SYNTHESIS; ENANTIOMERICALLY PURE; HOMOALLYLIC AMINES;

D O I：

10.1002/ejoc.200900787

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A stereodivergent synthesis of 2,3,5-trisubstituted pyrrolidines by an organocatalytic Mannich/aza-Michael addition sequence has been developed. Depending upon the choice of the base used in the intramolecular aza-Michael additions, 2,5-trans- or 2,5-cis-configured pyrrolidines were obtained in high yields and excellent diastereomeric ratios. Selective de-protection of the amino group and the side-chain hydroxy group proceeded without loss of diastereomeric purity. The stereodivergent outcome of the key aza-Michael reactions is the result of thermodynamically versus kinetically controlled cyclization, ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

引用

页码：5549 / 5564

页数：16

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