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

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	3039-3052
Nombre de pages	14
journal	Tetrahedron
Volume	45
Numéro de publication	10
Etat de la publication	Publié - 1 janv. 1989

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title = "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 = "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.",

author = "A. Krief and W. Dumont and P. Pasau and Ph. Lecomte",

year = "1989",

month = jan,

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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§. / Krief, A.; Dumont, W.; Pasau, P. et al.
Dans: Tetrahedron, Vol 45, Numéro 10, 01.01.1989, p. 3039-3052.

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

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T1 - Stereoselective synthesis of methyl (1R) trans- and (1R) cis-hemicaronaldehydes from natural tartaric acid

T2 - Application to the synthesis of s-bioallethrin and deltamethrin insecticides§

AU - Krief, A.

AU - Dumont, W.

AU - Pasau, P.

AU - Lecomte, Ph.

PY - 1989/1/1

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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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