Preparation of novel N-sulfonylated (S,S)-2,3-diaminosuccinatetype chiral auxiliaries and application to an asymmetric 1,3-dipolar cycloaddition reaction of nitrile oxides to allyl alcohol

摘要

Novel N-sulfonylated (S,S)-2,3-diaminosuccinate-type chiral auxiliaries, which have the tartaric acid-like framework with a sulfonamide group instead of a hydroxyl group, were synthesized from L-aspartic acid. The synthesized (S,S)-2,3-diaminosuccinate derivatives were applied to an asymmetric 1,3-dipolar cycloaddition reaction of nitrile oxides to allyl alcohol to afford the corresponding optically active 2-isoxazolines, with the enantioselectivities of up to 73% ee. The enantiofacial differentiation was intriguingly opposite to that by using diisopropyl tartrate as a chiral auxiliary. (c) 2006 Elsevier Ltd. All rights reserved.