Highly π-facial stereoselective aldol reaction of (S)-proline-derived amide enolate with benzaldehydes

Article abstract of DOI:10.1002/ejoc.200390097

The asymmetric aldol reaction of the (S)-proline-derived bicyclic amide enolate 1 with benzaldehydes selectively affords the two diastereomeric aldol adducts (3S,3′R,8S)-3a and (3S,3′S,8S)-3a, of four possible diastereomers, in good yield. The high control of π-facial stereoselectivity at the endocyclic C-3 stereocenter is due to perfect shielding by the pseudo-axial phenyl ring at the C-1 position. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.