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

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 journal › Article › peer-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 language	English
Pages (from-to)	3039-3052
Number of pages	14
Journal	Tetrahedron
Volume	45
Issue number	10
Publication status	Published - 1 Jan 1989

Cite this

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AB - 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.

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

Abstract

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