Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels−Alder Reactions through Hydrogen Bonding
- 12 January 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 127 (5) , 1336-1337
- https://doi.org/10.1021/ja044076x
Abstract
Axially chiral 1,1‘-biaryl-2,2‘-dimethanol (3, BAMOL) family of diols are highly effective catalysts for enantioselective hetero-Diels−Alder reactions between aminosiloxydiene 1 and a wide variety of unactivated aldehydes. The reactions proceed in useful yields and excellent enantioselectivities. The diols function in the same capacity as Lewis acids, by activating the aldehyde carbonyl group through hydrogen bonding.Keywords
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