An efficient synthesis of oxiranyl oxazolines and elaboration to acyl oxiranes

被引：11

作者：

Florio, S ^{[1
]}

Capriati, V ^{[1
]}

Di Martino, S ^{[1
]}

机构：

[1] Univ Bari, Dept Farmacochim, CNR, Ctr Studio Metodol Innovat Sintesi Organ, I-70125 Bari, Italy

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 31期

关键词：

deprotonation; oxiranyl oxazoline; oxazolinyl oxiranyllithium; oxazolidine; acyl oxirane;

D O I：

10.1016/S0040-4039(98)01096-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Deprotonation of oxazolinyl oxirane 1a with sec-BuLi/TMEDA at -100 degrees C in Et2O furnished oxazolinyl oxiranyllithium 1b, which could be trapped with electrophiles to give oxiranes 1c-g. The reaction of 1b with aldehydes produced diastereomers syn (2a-d) and anti (3a-d). Oxiranyllithium 1i from trans-1-oxazolinyl-2-p-tolyl epoxy ethane 1h was found to be configurationally stable while oxiranyllithium 11, generated from the cis isomer 1k, was not. Oxazolinyl epoxides 1d, 1j and 1m could be deblocked to acyl oxiranes 5a-e through oxazolidines 4a-e. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：5639 / 5642

页数：4

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