Chiral amide from (1S,2R)-(+)-norephedrine alkaloid in the enantioselective addition of diethylzinc to aryl and heteroaryl aldehydes

Chiral amide synthesized from (1S,2R)-(+)-norephedrine and furoic acid was found to catalyze the enantioselective ethylation of aromatic and heteroaromatic aldehydes to secondary alcohols with 99.8% enantioselectivity at 0 °C without the addition of a promoter such as titanium tetraisopropoxide.

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N-((1S,2R)-1-Hydroxy-1-phenylpropan-2-yl)furan-2-carboxamideC14H15NO3[α]D30=+70.4 (c 0.125, CHCl3)Source of chirality: (1S,2R)-(+)-norephedrineAbsolute configuration: (1S,2R)