Synthesis, atropoisomerism and chemistry of the dimers of R-(-)-carvone, R-(-)-hydrocarvone, 1R,5R-(+)-pinocarvone and other monoterpenic ketones

Authors
Mazzega, M Fabris, F Cossu, S De Lucchi, O Lucchini, V Valle, G
Citation
M. Mazzega et al., Synthesis, atropoisomerism and chemistry of the dimers of R-(-)-carvone, R-(-)-hydrocarvone, 1R,5R-(+)-pinocarvone and other monoterpenic ketones, TETRAHEDRON, 55(14), 1999, pp. 4427-4440
Citations number
35
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
14
Year of publication
1999
Pages
4427 - 4440
Database
ISI
SICI code
0040-4020(19990402)55:14<4427:SAACOT>2.0.ZU;2-F
Abstract
Oxidative homocoupling of R-(-)-carvone 4, R-(-)-hydrocarvone 21, 1R,5R-(+) -pinocarvone 25 and other monoterpenic ketones leads to the respective C-2- symmetric dimers 6, 20 and 26 in most cases as single diastereoisomers. Sub sequent reactions of dimeric compounds were investigated in detail. Other m onoterpenes (menthone. pulegone) undergo homocoupling in low yields and poo r diastereoselectivity. (C) 1999 Elsevier Science Ltd. All rights reserved.