Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels−Alder Reactions through Hydrogen Bonding
Journal of the American Chemical Society2005Vol. 127(5), pp. 1336–1337
Citations Over TimeTop 1% of 2005 papers
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.
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