Portal de Periódicos da CAPES

Axially Chiral Biaryl Diols Catalyze Highly Enantioselective Hetero-Diels−Alder Reactions through Hydrogen Bonding

2005; American Chemical Society; Volume: 127; Issue: 5 Linguagem: Inglês

10.1021/ja044076x

1943-2984

Aditya K. Unni, Norito Takenaka, Hisashi Yamamoto, Viresh H. Rawal,

Asymmetric Hydrogenation and Catalysis

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.