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.
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页码：4095 / 4099
页数：5
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