Synthesis of new 3,3-dimethoxyazetidine-2-carboxylic acid derivatives

被引：16
|
作者：
Mangelinckx, S
Boeykens, M
Vliegen, M
Van der Eycken, J
De Kimpe, N
机构：
[1] State Univ Ghent, Dept Organ Chem, Fac Agr & Appl Biol Sci, B-9000 Ghent, Belgium
[2] State Univ Ghent, Dept Organ Chem, Fac Sci, B-9000 Ghent, Belgium
来源：
TETRAHEDRON LETTERS | 2005年 / 46卷 / 03期
关键词：
azetidin-3-ones; azetidine-2-carboxylates; pyrrolidin-2-ones;
D O I：
10.1016/j.tetlet.2004.10.125
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Cyclization of gamma-amino-alpha-bromocarboxylic esters resulted in an efficient synthesis of new 3,3-dimethoxyazetidine-2-carboxylates, that is, methyl N-t-butyl-3,3-dimethoxyazetidine-2-carboxylic ester and 3,3-dimethoxyazetidine-2-carboxylic acid, or 3-bromo-4,4-dimethoxypyrrolidin-2-ones, depending on the substituent at nitrogen. Reduction of the 3,3-dimethoxyazetidine-2-carboxylates gave the corresponding 3,3-dimethoxy-2-(hydroxymethyl)azetidines. These novel cyclic amino acid derivatives. available-on multigram scale, have a suitably protected carbonyl function at the 3-position, which enables further functionalization. (C) 2004 Elsevier Ltd. All rights reserved.
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页码：525 / 529
页数：5
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