Remote substituent control of the regioselectivity of the aryl- and vinylpalladation of 7-oxabicyclo[2.2.1]heptenes

Remote substituent control of the regioselectivity of the aryl- and vinylpalladation of 7-oxabicyclo[2.2.1]heptenes

Montalbetti, C.; Savignac, M.; Genet, J. P.; Roulet, J. M.; Vogel, P.

1996

Formats

Format
BibTeX
MARCXML
TextMARC
MARC
DublinCore
EndNote
NLM
RefWorks
RIS

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 prefers the exo position of C(6) center.

Details

Title Remote substituent control of the regioselectivity of the aryl- and vinylpalladation of 7-oxabicyclo[2.2.1]heptenes

Author(s) Montalbetti, C. ; Savignac, M. ; Genet, J. P. ; Roulet, J. M. ; Vogel, P.

Published in Tetrahedron Letters

Volume 37

Issue 13

Pages 2225-2228

Date 1996

ISSN 0040-4039

Keywords

Asymmetric multipoint control; radical additions; palladium; derivatives; furan; prostaglandins; acrylonitrile; halides; analogs; acids

Note Ecole natl super chim,cnrs,organ synth lab,f-75231 paris 05,france. univ lausanne,chim sect,ch-1015 lausanne,switzerland.

DOI https://doi.org/10.1016/0040-4039(96)00237-7

Laboratories LGSA

Record Appears in Scientific production and competences > SB - School of Basic Sciences > SB Archives > LGSA - Laboratory of Glycochemistry and Asymmetric Synthesis
Peer-reviewed publications
Work produced at EPFL
Journal Articles
Published

Record creation date 2005-11-09