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

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.
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1996
Tetrahedron Letters

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.

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Type
research article
DOI
10.1016/0040-4039(96)00237-7
Author(s)
Montalbetti, C.
Savignac, M.
Genet, J. P.
Roulet, J. M.
Vogel, P.  
Date Issued

1996

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

37

Issue

13

Start page

2225

End page

2228

Subjects

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.

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LGSA  
Available on Infoscience
November 9, 2005
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/219717
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