Hydrogen bonding: Single enantiomers from a chiral-alcohol catalyst

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阅读量:

103

作者:

Y HuangAK UnniAN ThadaniVH Rawal

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摘要:

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.

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DOI:

10.1038/424146a

被引量:

791

年份:

2003

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来源期刊

Nature
July 2003

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2007
被引量:128

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