Highly stereoselective synthesis of optically active oxazolinyl oxiranes from azaenolates of a chiral 2-chloromethyloxazoline

被引：15

作者：

Florio, S ^{[1
]}

Capriati, V ^{[1
]}

Luisi, R ^{[1
]}

机构：

[1] Univ Bari, Dipartimento Farm Chim, Ctr Studio Metodol Innovat Sintesi Organ, CNR, I-70125 Bari, Italy

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 27期

关键词：

boron azaenolate; titanium azaenolate; chiral oxazolines; chiral oxiranyl oxazolines;

D O I：

10.1016/S0040-4039(00)00809-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Boron and titanium azaenolates 2 and 4, generated at 0 degrees C and -100 degrees C, respectively, from the optically active chloromethyloxazoline 1, have been found to couple with aliphatic ketones in a highly diastereoselective fashion ending up with the formation of optically active oxazolinyl oxiranes 3. Less stereoselective was the reaction with aromatic ketones. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5295 / 5298

页数：4

共 11 条

[1]

ANNUNZIATA R, 1983, SYNTHESIS-STUTTGART, P1016

[2] PREPARATION OF FUNCTIONALIZED OXAZOLINES [J].