One-pot diastereoselective synthesis of 2-acyl-4-nitrocyclohexanol derivatives in aqueous medium

被引：19

作者：

Ballini, R

Barboni, L

Bosica, G

Filippone, P

Peretti, S

机构：

[1] Univ Camerino, Dipartimento Sci Chim, I-62032 Camerino, Italy

[2] Fac Sci, Ist Chim Organ, I-61029 Urbino, Italy

来源：

TETRAHEDRON | 2000年 / 56卷 / 24期

关键词：

diastereoselection; nitro compounds; cyclisation; reaction in water;

D O I：

10.1016/S0040-4020(00)00324-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of primary nitroalkanes with conjugated enones, in water and in the presence of K2CO3 as base, allows the synthesis of 2-acyl-4-nitrocyclohexanol derivatives in which the diastereoisomer (+/-)-(1S*,2R*,5R) is highly pre dominant. The reaction proceeds by double Michael addition of the nitroalkane to the enone, followed by intramolecular aldol reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：4095 / 4099

页数：5

共 14 条

[1]

Ballini R, 1998, EUR J ORG CHEM, V1998, P355, DOI 10.1002/(SICI)1099-0690(199802)1998:2<355::AID-EJOC355>3.0.CO

[2]

2-2

[3] The Michael reaction of nitroalkanes with conjugated enones in aqueous media [J].