METAL DIRECTED STEREOSELECTIVE SYNTHESIS OF 3-(1'-HYDROXYETHYL)-2-AZETIDINONES FROM ETHYL 3-HYDROXYBUTYRATE

被引：11

作者：

GEORG, GI

AKGUN, E

机构：

[1] Department of Medicinal Chemistry University of Kansas, Lawrence

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(00)89040-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The enolate-imine condensation of the lithio dianion 8 of ethyl 3-hydroxybutyrate 7 with N-anisylcinnamylideneimine was studied in the presence of a variety of metal salts and organometallic reagents. Addition of tert-butyl magnesium chloride to the reaction mixture produced the rel(1′R,3R,4S)-3-(1′hydroxyethyl)-2-azetidinone 9, whereas the addition of triethylborane gave solely the rel(1′R,3R,4R) derivative 10. © 1990.

引用

页码：3267 / 3270

页数：4

共 11 条

[1]

BENTLY PH, 1989, ADV CHEM BETA LACTAM

[2]

BROWN MJ, 1989, HETEROCYCLES, V29, P2225

[3]

Georg G. I., 1989, STUDIES NATURAL PROD, V4, P4331

[4]

GEORG GI, 1985, TETRAHEDRON LETT, V26, P3903, DOI 10.1016/S0040-4039(00)98683-0