U-4C-3CR versus U-5C-4CR and stereochemical outcomes using suitable bicyclic β-amino acid derivatives as bifunctional components in the Ugi reaction

被引：47

作者：

Basso, A ^{[1
]}

Banfi, L ^{[1
]}

Riva, R ^{[1
]}

Guanti, G ^{[1
]}

机构：

[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 03期

关键词：

multicomponent reactions; intramolecular Ugi reaction; beta-amino acids; chiral auxiliary; stereoselective Ugi reaction; Ugi with secondary amines;

D O I：

10.1016/j.tetlet.2003.10.193

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular Ugi reactions with bicyclic beta-amino acids have been performed and the effects of the configuration and N-alkylation have been studied. We have proven that preferential ring contraction or nucleophilic attack by the solvent depend not only on the presence of N-alkylation but also on the relative disposition of the carboxyl group and the amine. Excellent results in terms of stereoselectivity have been obtained in the case of N-alkyl-3-exo-amino-7-oxabicyclo[2.2.1]-2-endo-carboxylic acids. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：587 / 590

页数：4

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