ENANTIOSELECTIVE ALLYLIC SUBSTITUTIONS USING KETENE SILYL ACETALS CATALYZED BY A PALLADIUM-CHIRAL AMIDINE COMPLEX

Authors
SAITOH A ACHIWA K MORIMOTO T
Citation
A. Saitoh et al., ENANTIOSELECTIVE ALLYLIC SUBSTITUTIONS USING KETENE SILYL ACETALS CATALYZED BY A PALLADIUM-CHIRAL AMIDINE COMPLEX, Tetrahedron : asymmetry, 9(5), 1998, pp. 741-744
Citations number
33
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
9
Issue
5
Year of publication
1998
Pages
741 - 744
Database
ISI
SICI code
0957-4166(1998)9:5<741:EASUKS>2.0.ZU;2-S
Abstract
Enantioselective allylic substitutions using ketene silyl acetals 3 as a nucleophile have been explored. In the asymmetric reactions of 1,3- diphenylprop-2-enyl pivalate 2 catalyzed by the Pd(O)-chiral amidine 1 complex, excellent levels of stereocontrol are achieved along with go od conversions, demonstrating that ketene silyl acetals are able to ex pand the scope of asymmetric allylic alkylations. The present asymmetr ic reactions should proceed via nucleophilic attack at the allyl termi nus trans to the diphenylphosphinyl group of the amidine on the side o pposite to palladium. (C) 1998 Elsevier Science Ltd. All rights reserv ed.