Brief Communications

Nature 424, 146 (10 July 2003) | doi:10.1038/424146a

Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst

Yong Huang1, Aditya K. Unni1, Avinash N. Thadani1 & Viresh H. Rawal1

Hydrogen bonding acts as a ubiquitous glue to sustain the intricate architecture and functionality of proteins, nucleic acids and many supramolecular assemblies1, 2, but this weak interaction is seldom used as a force for promoting chemical reactions3, 4, 5. Here we show that a simple chiral alcohol uses hydrogen bonding to catalyse an important family of cycloaddition reactions of a diene with various aldehydes — moreover, this reaction is highly enantioselective, generating only one of the mirror-image forms of each dihydropyran product. This type of catalysis mimics the action of enzymes and antibodies, and is unlike traditional, metal-based catalysts used in organic chemistry6.

  1. Department of Chemistry, University of Chicago, Chicago, Illinois 60637, USA

Correspondence to: Viresh H. Rawal1 Email: vrawal@uchicago.edu