Premium
Synthesis and Application of Chiral Phospholane Ligands Bearing a Sterically and Electrically Adjustable Moiety
Author(s) -
Matsumura Kazuhiko,
Shimizu Hideo,
Saito Takao,
Kumobayashi Hidenori
Publication year - 2003
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200390008
Subject(s) - steric effects , chemistry , moiety , substituent , aryl , catalysis , phosphine , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , alkyl
A series of C 1 ‐symmetric phosphine‐phospholane ligands, 1‐(disubstituted phosphino)‐2‐(phospholano)benzenes ( 5 ), which are called UCAPs, with an achiral phosphino group and a chiral phospholane which can be sterically and electrically adjustable, has been designed and synthesized. In the asymmetric hydrogenation of ( Z )‐ N ‐benzoyl‐1‐phenylpropenamine ( 3 ), the stereorecognition abilities of the 5d−e –Rh catalysts which have a bulkier aryl substituent on the achiral phosphorus are superior to that observed with the DuPHOS‐Rh catalyst. The effects of varying substituents on the achiral phosphorus atom are discussed.