ASYMMETRIC HALOLACTONISATION REACTION-4 ASYMMETRIC SYNTHESIS OF OPTICALLY ACTIVE α,β-EPOXYALDEHYDES FROM α,β-UNSATURATED ACIDS

Article abstract of DOI:10.1016/S0040-4020(01)92348-8

The bromolactones (5) stereoselectively produced by the asymmetric bromolactonisation of (S)-N-(α,β-unsaturated)acylprolines (3), were elaborated to highly optically active 2(R),3(S)-epoxyaldehydes (8) (84-98percent ee) by successive epoxide formation and reductive cleavage of the proline moiety.The overall process constitutes a highly efficient asymmetric synthesis of 8 from α,β-unsaturated acids (1).