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Bifunctional Binols: Chiral 3,3′‐Bis(aminomethyl)‐1,1′‐bi‐2‐naphthols (Binolams) in Asymmetric Catalysis
Author(s) -
Nájera Carmen,
Sansano José M.,
Saá José M.
Publication year - 2009
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/ejoc.200801069
Subject(s) - enantioselective synthesis , chemistry , bifunctional , nucleophile , cyanation , electrophile , catalysis , combinatorial chemistry , reagent , nucleophilic addition , organic chemistry , stereochemistry , medicinal chemistry
3,3′‐Bis(dialkylaminomethyl)‐1,1′‐binaphth‐2‐ols (Binolams) have emerged during the last five years as very efficient chiral ligands in many enantioselective processes. Enantiomerically pure Binolams are easily accessible by means of a variety of methods, the most widely used being the so‐called chiral Binol route. In most cases, Binolam‐metal complexes behave as bifunctional catalysts: that is, they are characterized by their dual action on the reagents, being able to activate both the nucleophilic and the electrophilic species involved in the reaction. The most successful transformations carried out with complexes of this type include cyanation of aldehydes and ketones and enantioselective nucleophilic additions of enolate derivatives and organometallic compounds to C=O or C=N double bonds. As a final bonus, the basic natures of these ligands allow their recovery in high yields in numerous transformations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)