Single enantiomers from a chiral-alcohol catalyst

Yong Huang, Aditya K. Unni, Avinash N. Thadani and Viresh H. Rawal ()
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Yong Huang: University of Chicago
Aditya K. Unni: University of Chicago
Avinash N. Thadani: University of Chicago
Viresh H. Rawal: University of Chicago

Nature, 2003, vol. 424, issue 6945, 146-146

Abstract: Abstract 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.

Date: 2003
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DOI: 10.1038/424146a

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