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Enantioselective Addition of Organozinc Reagents to Aldehydes Catalyzed by 3,3′‐Bis(diphenylphosphinoyl)‐BINOL
Author(s) -
Hatano Manabu,
Miyamoto Takashi,
Ishihara Kazuaki
Publication year - 2005
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.200505221
Subject(s) - chemistry , enantioselective synthesis , reagent , catalysis , nucleophile , thio , medicinal chemistry , organic chemistry , combinatorial chemistry
The enantioselective addition of organozinc reagents to aromatic and aliphatic aldehydes 1 gives secondary alcohols 2 with excellent enantioselectivities in high yields through the catalytic use of ( R )‐3,3′‐bis(diphenylphosphinoyl)‐BINOL ( 3 ) or ( R )‐3,3′‐bis(diphenylthiophosphinoyl)‐BINOL ( 4 ) without Ti(IV) complexes. The coordination of the O or S atom of a (thio)phosphinoyl group bearing a BINOL backbone to organozinc reagents can efficiently increase the nucleophilicity of the organozinc reagents.