Synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates and alkyl 3-bromoazetidine-3-carboxylates as amino acid building blocks

被引：25
作者：
Mangelinckx, Sven [1 ]
Zukauskaite, Asta [2 ]
Buinauskaite, Vida [2 ]
Sackus, Algirdas [2 ]
De Kimpe, Norbert [1 ]
机构：
[1] Univ Ghent, Dept Organ Chem, Fac Biosci Engn, B-9000 Ghent, Belgium
[2] Kaunas Univ Technol, Fac Chem Technol, Dept Organ Chem, LT-50270 Kaunas, Lithuania
来源：
TETRAHEDRON LETTERS | 2008年 / 49卷 / 48期
关键词：
Aziridine-2-carboxylates; Azetidine-3-carboxylates; Ring closure; 2-(Bromomethyl)aziridines; 3-Bromoazetidines;
D O I：
10.1016/j.tetlet.2008.09.119
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A short synthesis of alkyl 2-(bromomethyl)aziridine-2-carboxylates and alkyl 3-bromoazetidine-3-carboxylates was developed involving amination, bromination, and base-induced cyclization of alkyl 2-(bromomethyl)acrylates. These new small ring azaheterocyclic alpha- and beta-amino acid derivatives are promising synthons as demonstrated by their transformation to 2-(aminomethyl)aziridine-2-carboxylates and 3-aminoazetidine-3-carboxylates. (c) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6896 / 6900
页数：5
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