Single enantiomers from a chiral-alcohol catalyst
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TL;DR
It is shown that a simple chiral alcohol uses hydrogen bonding to catalyse an important family of cycloaddition reactions of a diene with various aldehydes, which is highly enantioselective, generating only one of the mirror-image forms of each dihydropyran product.
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.