Asymmetric synthesis of 4-substituted prolines as conformationally constrained amino acid analogues

Article abstract of DOI:10.1016/S0040-4020(98)00989-2

Treatment of readily available chiral building block 1 with (2R)-2,3-O- isopropylideneglyceraldehyde (5) provides a new route for asymmetric synthesis of 2,4-disubstituted pyrrolidines. Several proline-amino acid chimeras: proline-leucine, proline-lysine, proline-arginine and proline- glutamic acid, are synthesized in highly diastereomerically pure forms.