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trans ‐Chelating Chiral Diphosphane Ligands Bearing Flexible P ‐Alkyl Substituents (AlkylTRAPs) and their Application to the Rhodium‐Catalyzed Asymmetric Hydrosilylation of Simple Ketones
Author(s) -
Sawamura Masaya,
Kuwano Ryoichi,
Ito Yoshihiko
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199401111
Subject(s) - hydrosilylation , acetophenone , rhodium , alkyl , chemistry , catalysis , medicinal chemistry , ligand (biochemistry) , chelation , stereochemistry , organic chemistry , receptor , biochemistry
Not bulky substituents but flexible alkyl groups led to the hitherto highest enantioselectivities for the asymmetric hydrosilylation of simple ketones catalyzed by diphosphanerhodium complexes. The reduction of acetophenone in the presence of the diphosphane ligand 1 , R = n Pr, n Bu, gave 92% ee , whereas with 1 , R = Ph and R = i Pr, ee values of only 15% and 1%, respectively, were achieved.