Asymmetric -Wittig Rearrangement Involving a Chiral Ester Enolate Terminus. A Chiral Synthesis of erythro-α-Hydroxy-β-alkyl Carboxylic Acid Derivatives

Article abstract of DOI:10.1246/cl.1987.69

The title rearrangement of the (E-2-alkenyloxy)acetic esters derived from (-)-8-phenylmenthol has been shown to afford the corresponding 3-alkyl-2-hydroxy-4-pentenoic ester with an extremly high level of diastereoface selection (95-97percent de) along with a high erythro selectivity (90-93percent).