Fluoroolefin dipeptide isosteres - II. Enantioselective synthesis of both antipodes of the Phe-Gly dipeptide mimic

Article abstract of DOI:10.1016/S0040-4039(00)88549-4

The addition of optically active ester enolatas to α-fluoro-α,β-unsaturated aldehydes and formal S_N2′ substitution of an allylic hydroxyl group thus formed by a trichloro-acetamido group via Overman rearrangement constitutes a new general route to fluoroofefin dipeptide isosteres in enantiomerically pure form. This methodology was applied for the preparation of both enantiomars of the Phe...(CF=CH)Gly dipeptide mimic which were further elongated to substance P analogues.