UNSYMMETRICAL FUNCTIONALIZATION OF 1,3-CYCLOHEXADIENES - PALLADIUM-CATALYZED STEREOSELECTIVE 1,4-ACYLOXY-ALKOXYLATION

Authors
HUPE E ITAMI K ARANYOS A SZABO KJ BACKVALL JE
Citation
E. Hupe et al., UNSYMMETRICAL FUNCTIONALIZATION OF 1,3-CYCLOHEXADIENES - PALLADIUM-CATALYZED STEREOSELECTIVE 1,4-ACYLOXY-ALKOXYLATION, Tetrahedron, 54(20), 1998, pp. 5375-5384
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
20
Year of publication
1998
Pages
5375 - 5384
Database
ISI
SICI code
0040-4020(1998)54:20<5375:UFO1-P>2.0.ZU;2-Z
Abstract
Palladium-catalyzed reaction of 1,3-cyclohexadiene with alcohols and a cetic or benzoic acid under mild acidic conditions gives trans-1-aceto xy- or trans-1-benzyloxy-4-alkoxy-2-cyclohexenes, respectively, with h igh regio-and stereo-selectivity. The unsymmtrical 1,4-acyloxy-alkoxy products are obtained by fine tuning the reaction conditions in a narr ow pH range. (C) 1998 Elsevier Science Ltd. All rights reserved.