On the coupling reaction of lithium azaenolates of chiral oxazolines with carbonyl compounds

被引：20

作者：

Florio, S

Capriati, V

Luisi, R

Abbotto, A

Pippel, DJ

机构：

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

[2] Univ Milano Bicocca, Dipartimento Sci Mat, I-20125 Milan, Italy

[3] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

TETRAHEDRON | 2001年 / 57卷 / 31期

关键词：

lithium and compounds; enolates; oxazolines; epoxides; computer-assisted methods;

D O I：

10.1016/S0040-4020(01)00611-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Optically pure chloromethyloxazolines have been prepared, lithiated and then reacted with benzophenone to famish stereoselectively oxazolinyl oxiranes and formyl oxiranes. The stereoselection observed has been related to the geometry of the intermediate lithium azaenolates. Calculations have been carried out in order to evaluate the relative stability of the E and Z forms of the lithium azaenolates. The reaction of a lithium azaenolate with other ketones leading to oxazolinyl epoxides is also reported. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6775 / 6786

页数：12

共 37 条

[1] Ab initio and semiempirical study of the effect of ethereal solvent on aggregation of a lithium enolate [J].