(S)-proline-derived chiral ligands bearing organosulfur or -selenenyl groups as coordinating elements in palladium-catalyzed asymmetric allylic alkylations

Citation
Y. Suzuki et al., (S)-proline-derived chiral ligands bearing organosulfur or -selenenyl groups as coordinating elements in palladium-catalyzed asymmetric allylic alkylations, HETEROCYCLE, 50(1), 1999, pp. 89-94
Citations number
33
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
50
Issue
1
Year of publication
1999
Pages
89 - 94
Database
ISI
SICI code
0385-5414(19990101)50:1<89:(CLBOO>2.0.ZU;2-L
Abstract
(S)-Proline-derived chiral ligands bearing organosulfur or -selenenyl group s as coordinating elements were synthesized, and applied to palladium-catal yzed asymmetric allylic alkylations. These heteroatoms in the ligands playe d a prominent role for the stereocontrol of the conformation of the interme diary palladium complexes, and resultingly for the presentation of the high asymmetric induction in the asymmetric alkylations. The mechanism of the a symmetric synthesis using these ligands is rationalized on the basis of the stereochemical outcome observed.