Oxazolinyloxiranyllithium-mediated synthesis of highly strained heterocyclic compounds

被引：9

作者：

Luisi, R ^{[1
]}

Capriati, V ^{[1
]}

Degennaro, L ^{[1
]}

Florio, S ^{[1
]}

机构：

[1] Univ Bari, Dipartimento Farmacochim, Ist Chim Composti Organometall ICCOM, CNR,Sezione Bari, I-70126 Bari, Italy

来源：

TETRAHEDRON | 2003年 / 59卷 / 49期

关键词：

oxazolines; oxiranes; lithiation; nitrones; spiro compounds;

D O I：

10.1016/j.tet.2003.09.017

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition reaction of alpha-lithiated oxazolinyloxiranes to nitrones has been investigated. 1,5,9-Trioxa-8,10-diazadispiro[2.0.4.3]undecanes formed in a completely diastereoselective manner upon treatment of alpha-lithiated oxiranes with nitrones. The lithiation of optically active trans and cis-oxazolinyloxiranes followed by the addition of a nitrone resulted in the formation of the same dispirocyclic compound. An explanation for the observed stereoselectivity is provided. (C) 2003 Elsevier Ltd. All rights reserved.

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页码：9713 / 9718

页数：6

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