Stereoselective synthesis of methyl (1R) trans- and (1R) cis-hemicaronaldehydes from natural tartaric acid: Application to the synthesis of s-bioallethrin and deltamethrin insecticides§

A. Krief, W. Dumont, P. Pasau, Ph. Lecomte

    Research output: Contribution to journalArticlepeer-review

    Abstract

    Very efficient enantioselective syntheses of (1R)-trans-and cis-hemicaronaldehydes precursors of (1R)-trans chrysanthemic acid and its (1R)-cis dibromovinyl analogue starting from natural tartaric acid or D-mannitol are described. They are based on the reaction between isopropylidenetriphenylphosphorane or isopropylidenediphenylsulfurane and chiral γ-alkoxy-α,β-unsaturated esters. The general problem of the diastereoselective addition to such esters is discussed.
    Original languageEnglish
    Pages (from-to)3039-3052
    Number of pages14
    JournalTetrahedron
    Volume45
    Issue number10
    Publication statusPublished - 1 Jan 1989

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