Synthesis of cyclobutane serine analogues

被引：33

作者：

Avenoza, A ^{[1
]}

Busto, JH ^{[1
]}

Canal, N ^{[1
]}

Peregrina, JM ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 01期

关键词：

D O I：

10.1021/jo048943s

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this paper, we describe a thermal [2 + 2] cycloaddition involving 2-acylaminoacrylates as electron-poor acceptor alkenes, a reaction that involves a Michael-Dieckmann-type process. The reaction gives rise to a new substituted cyclobutane skeleton that can be transformed into amino acid derivatives. For example, a number of transformations were carried out to give the two pairs of stereoisomers of the 2-hydroxycyclobutane-alpha-amino acid serine analogue (C(4)Ser); compounds 22 and 23. This synthesis covers a gap in knowledge in the broad field of restricted amino acids.

引用

页码：330 / 333

页数：4

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