N-(2-Hydroxyacetyl)pyrrole as an Ester Surrogate in Asymmetric Mannich Reactions

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N-(2-Hydroxyacetyl)pyrrole underwent a direct Mannich reaction with a variety of o-Ts aldimines to afford predominantly a syn-α-hydroxy-β-amino amide in good to excellent yield. Good diastereoselectivity and high enantionselectivity were achieved by using In(Oi-Pr)3 and (S,S)-linked BINOL as the catalyst system. Chiral aminoalcohols are important building blocks for many natural products and pharmaceuticals. As an ester equivalent, the N-acyl amide can be easily transformed to many common functional groups such as esters, alkyl amides, aldehydes.