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Cobalt‐Catalyzed Addition Reaction of Organoboronic Acids with Aldehydes: Highly Enantioselective Synthesis of Diarylmethanols
Author(s) -
Karthikeyan Jaganathan,
Jeganmohan Masilamani,
Cheng ChienHong
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201001160
Subject(s) - enantioselective synthesis , enantiomer , enantiomeric excess , catalysis , chemistry , ligand (biochemistry) , pentane , cobalt , combinatorial chemistry , organic chemistry , medicinal chemistry , biochemistry , receptor
Predicted outcomes : The addition reaction of organoboronic acids with aldehydes in the presence of K 2 CO 3 catalyzed by CoI 2 /( R , R )‐BDPP gives chiral secondary alcohols in excellent yields with 90–99 % enantiomeric excess (see scheme; ( R , R )‐BDPP=(2 R ,4 R )‐(+)‐2,4‐bis(diphenylphosphino)pentane). This method provides an alternative to prepare an R and S enantiomeric pair by using the same chiral ligand and allows the stereochemical outcome of the reaction to be predicted.