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Paper

Chem. Commun., 1996, 1953 - 1954, DOI: 10.1039/CC9960001953

Asymmetry in the boronic acid Mannich reaction: diastereocontrolled addition to chiral iminium species derived from aldehydes and (S)-5-phenylmorpholin-2-one

Laurence M. Harwood, Gordon S. Currie, Michael G. B. Drew and Richard W. A. Luke

(S)-5-Phenylmorpholin-2-one and a range of aliphatic aldehydes form chiral iminium intermediates which undergo diastereoselective Mannich reactions with 2-furylboronic acid. Single crystal X-ray analysis of methylated derivative 4 derived from major adduct 2g confirms the stereochemical course of the reaction.