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- Title
Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst.
- Authors
Huang, Yong; Unni, Aditya K.; Thadani, Avinash N.; Rawal, Viresh H.
- Abstract
Hydrogen bonding acts as a ubiquitous glue to sustain the intricate architecture and functionality of proteins, nucleic acids and many supramolecular assemblies, but this weak interaction is seldom used as a force for promoting chemical reactions. 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 chemistry.
- Subjects
HYDROGEN bonding; CHEMICAL reactions; CATALYSIS; ENZYMES; ORGANIC chemistry
- Publication
Nature, 2003, Vol 424, Issue 6945, p146
- ISSN
0028-0836
- Publication type
Article
- DOI
10.1038/424146a