Synthesis of 2-methyl- and 2-methylenecyclobutane amino acids

被引：19

作者：

Avenoza, A ^{[1
]}

Busto, JH ^{[1
]}

Peregrina, JM ^{[1
]}

Pérez-Fernández, M ^{[1
]}

机构：

[1] Univ La Rioja, Dept Quim, Grp Sintesis Quim Rioja, CSIC, E-26006 Logrono, Spain

来源：

TETRAHEDRON | 2005年 / 61卷 / 16期

关键词：

amino acid; cyclobutane; hydrogenation; valine;

D O I：

10.1016/j.tet.2005.02.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient and easy formal [2+2] cycloaddition (Michael-Dieckmann-type reaction) on methyl 2-acetamidoacrylate with ketene diethyl acetal gave the cyclobutane core. Two kinds of 2-substituted cyelobutane amino acids have been obtained from this compound by means of stereocontrolled interconversion of functional groups: 1-amino-2-methylcyclobutane-1-carboxylic acids (2,4-methanovalines) and 1-amino-2-methylenecyclobutane-1-carboxylic acid. The latter amino acid can be regarded as a restricted a-methyl-a-vinylglycine. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：4165 / 4172

页数：8

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