Stereoselective synthesis of pyrrolidinyl glycines from nitrones:: complementarity of nucleophilic addition and 1,3-dipolar cycloaddition

被引：16

作者：

Merino, Pedro ^{[1
]}

Padar, Petra

Delso, Ignacio

Thirumalaikumar, Muniappan

Tejero, Tomas

Kovacs, Lajos

机构：

[1] Univ Zaragoza, Inst Ciencia Mat Aragon, Dept Quim Organ, Lab Sintesis Asimetr,CSIC, E-50009 Zaragoza, Spain

[2] Univ Szeged, Dept Med Chem, H-6720 Szeged, Hungary

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 29期

关键词：

D O I：

10.1016/j.tetlet.2006.05.114

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Epimeric pyrrolidinyl glycines, a sort of conformation ally constrained alpha,beta-diaminoacids, were stereoselectively prepared using complementary approaches based on nitrone chemistry. Nucleophilic additions to pyrrolidinyl nitrones and 1,3-dipolar cycloadditions Of L-serine derived nitrones to form the corresponding hydroxylamines and isoxazolidines, respectively, provided key intermediates for the synthesis of the target compounds. Whereas the nucleophilic addition route afforded the syn adduct, the 1,3-dipolar cycloaddition approach furnished the precursor for the preparation of the corresponding anti compound. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5013 / 5016

页数：4

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