CHIRALITY TRANSFER IN PALLADIUM-CATALYZED REACTIONS OF ALLYLAMMONIUM SALTS

Authors
DOI T YANAGISAWA A MIYAZAWA M YAMAMOTO K
Citation
T. Doi et al., CHIRALITY TRANSFER IN PALLADIUM-CATALYZED REACTIONS OF ALLYLAMMONIUM SALTS, Tetrahedron : asymmetry, 6(2), 1995, pp. 389-392
Citations number
39
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
2
Year of publication
1995
Pages
389 - 392
Database
ISI
SICI code
0957-4166(1995)6:2<389:CTIPRO>2.0.ZU;2-X
Abstract
Optically active 1-isobutyl-2(Z)-butenyltrimethylammonium iodide (10) underwent allylation with dimethyl sodiomalonate in the presence of a palladium(0) catalyst. The reaction proceeded predominantly with 1,3 t ransposition and with inversion of configuration due probably to a pri or isomerization from anti to syn-pi-allylpalladium intermediate (14-- >15). The stereochemistry observed in the reaction with phenylzinc chl oride was opposite to that with the soft nucleophile.