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

Authors
Ballini, R Barboni, L Bosica, G Filippone, P Peretti, S
Citation
R. Ballini et al., One-pot diastereoselective synthesis of 2-acyl-4-nitrocyclohexanol derivatives in aqueous medium, TETRAHEDRON, 56(24), 2000, pp. 4095-4099
Citations number
13
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
24
Year of publication
2000
Pages
4095 - 4099
Database
ISI
SICI code
0040-4020(20000609)56:24<4095:ODSO2D>2.0.ZU;2-7
Abstract
The reaction of primary nitroalkanes with conjugated enones, in water and i n the presence of K2CO3 as base, allows the synthesis of 2-acyl-4-nitrocycl ohexanol derivatives in which the diastereoisomer (+/-)-(1S*,2R*,5R) is hig hly pre dominant. The reaction proceeds by double Michael addition of the n itroalkane to the enone, followed by intramolecular aldol reaction. (C) 200 0 Elsevier Science Ltd. All rights reserved.