INTRAMOLECULAR PD-CATALYZED ARYL-ENONE CONJUGATE ADDITIONS - CONTROL OF REDUCTIVE VS NONREDUCTIVE CYCLIZATION

Authors
FRIESTAD GK BRANCHAUD BP
Citation
Gk. Friestad et Bp. Branchaud, INTRAMOLECULAR PD-CATALYZED ARYL-ENONE CONJUGATE ADDITIONS - CONTROL OF REDUCTIVE VS NONREDUCTIVE CYCLIZATION, Tetrahedron letters, 36(39), 1995, pp. 7047-7050
Citations number
50
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
36
Issue
39
Year of publication
1995
Pages
7047 - 7050
Database
ISI
SICI code
0040-4039(1995)36:39<7047:IPACA->2.0.ZU;2-5
Abstract
Pd-catalyzed aryl-enone cyclization of 1 leads to Heck-type non-reduct ive cyclization product 3 and reductive cyclization product 4. Conditi ons have been developed to selectively form either 3 or 4 (or more hig hly functionalized 10 vs 11 or 13 vs 14). The formation of non-reducti ve cyclization products (3, 11, 14) requires an unusual apparent trans beta-H elimination - some mechanistic possibilities that are consiste nt with the data are proposed.