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Chiral ( o ‐Hydroxyaryl)oxazaphospholidine Oxides: A New Class of Bifunctional Catalysts in the Enantioselective Borane Reduction of Ketones
Author(s) -
Brunel Jean Michel,
Legrand Olivier,
Buono Gérard
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200010)2000:19<3313::aid-ejoc3313>3.0.co;2-m
Subject(s) - borane , chemistry , bifunctional , enantioselective synthesis , moiety , catalysis , enantiomer , ketone , enantiomeric excess , organic chemistry , bifunctional catalyst , combinatorial chemistry
The synthesis of a new class of bifunctional organophosphorus catalysts for the asymmetric borane reduction of prochiral ketones has been investigated. Keys to the architecture of effective catalysts are an oxazaphospholidine structural unit and a hydroxyaryl moiety. These ( o ‐hydroxyaryl)oxazaphospholidine oxides have been successfully applied to the catalytic (2 mol‐%) asymmetric borane reduction of numerous prochiral ketones with enantiomeric excesses up to 84% ee .