On the lithiation of oxazolinylaziridines

被引：33

作者：

Luisi, R

Capriati, V

Florio, S

Ranaldo, R

机构：

[1] Univ Bari, Dipartimento Farmacochim, I-70126 Bari, Italy

[2] CNR, ICCOM, Sez Bari, Bari, Italy

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 13期

关键词：

D O I：

10.1016/S0040-4039(03)00368-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiated N-sulfonyloxazolinylaziridines 6a and 7a, generated by deprotonation of the corresponding aziridines 6 and 7 with sec-BuLi/TMEDA at -98degreesC in THF, were found to be chemically and configurationally stable to be stereospecifically captured by electrophiles, while warming up to rt resulted in the formation of oxazolinylazirine 15. In contrast, lithiation of N-phetiyloxazolinylaziridines 8 and 9 led to oxazolinylenamine 18. Tricyclic aziridines 10 and 11 resulted from an intramolecular addition of the aziridinyllithium 6a to the phenyl ring of the benzenesulfonyl group. (C) 2003 Elsevier Science Ltd. All rights reserved.

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页码：2677 / 2681

页数：5

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