REMOTE SUBSTITUENT CONTROL OF THE REGIOSELECTIVITY OF THE ARYLPALLADATION AND VINYLPALLADATION OF 7-OXABICYCLO[2.2.1]HEPTENES

Authors
MONTALBETTI C SAVIGNAC M GENET JP ROULET JM VOGEL P
Citation
C. Montalbetti et al., REMOTE SUBSTITUENT CONTROL OF THE REGIOSELECTIVITY OF THE ARYLPALLADATION AND VINYLPALLADATION OF 7-OXABICYCLO[2.2.1]HEPTENES, Tetrahedron letters, 37(13), 1996, pp. 2225-2228
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
13
Year of publication
1996
Pages
2225 - 2228
Database
ISI
SICI code
0040-4039(1996)37:13<2225:RSCOTR>2.0.ZU;2-V
Abstract
Pd-catalyzed arylations of 2-exo-cyano-7-oxabicyclo[2.2.1]hept-5-en-2- endo-yl acetate and 7-oxabicycio[2.2.1]hept-5-en-2-one are regio- and stereoselective giving products of H-2(HCOOH) and Me(3)SiC=H coupling in which the aryl group (4-MeOC(6)H(4)) prefers the exo position of C( 5) whereas the Pd-catatyzed vinylations with methyl-2-iodoacrylate pre fers the exo position of C(6) center.