Enantioselective nucleophilic catalysis with "Planar-Chiral" heterocycles.
Although Lewis bases (e.g., tertiary phosphines, tertiary amines, and pyridines) serve as nucleophilic catalysts for a wide array of reactions, there have been relatively few reports of enantioselective nucleophilic catalysts. In this Account, we describe the design and synthesis of a new family of chiral nucleophilic catalysts, specifically, planar-chiral heterocycles. These complexes provide good levels of enantiomeric excess in the addition of alcohols to ketenes, the rearrangement of O-acylated azlactones, and the kinetic resolution of secondary alcohols.
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Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
D000438:Alcohols / Q000737:chemistry; D002384:Catalysis; D005296:Ferrous Compounds / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D000438:Alcohols; D005296:Ferrous Compounds; D006571:Heterocyclic Compounds; D007659:Ketones