STEREOSELECTIVE SYNTHESIS OF 3-(ETHOXYCARBONYL)-4-HYDROXY-5-(1-HYDROXYALKYL)-2-ISOXAZOLINE 2-OXIDES BY REACTION OF 2,3-EPOXY ALDEHYDES AND ETHYL NITROACETATE ON ALUMINA SURFACE

被引：74

作者：

ROSINI, G

GALARINI, R

MAROTTA, E

RIGHI, P

机构：

[1] Dipartimento di Chimica Organica, “A. Mangini” Universita, 4.1 40136 Bologna, Viale Risorgimento

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1990年 / 55卷 / 03期

关键词：

D O I：

10.1021/jo00290a001

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

: Treatment of racemic 2,3-epoxy aldehydes and ethyl nitroacetate with alumina affords title compounds through a nitroaldol reaction—cyclization process. While in the case of 3-trans-monosubstituted substrates, C4,C5-trans and cis isomers (dr = 1.5) with C5,C6-anti configuration are obtained, 3-cis-monosubstituted 2,3-epoxy aldehydes give C4,C5-trans and cis derivatives with a much higher diastereoselectivity (dr > 20) and C5,C6-syn configuration. 5-Exo cyclization occurs also when 2,3-epoxy aldehydes are 2-substituted. © 1990, American Chemical Society. All rights reserved.

引用

页码：781 / 783

页数：3

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