Asymmetric synthesis of long chain α-methyl-β-thiotrifluoromethyl ketones employing the SAMP-/RAMP-hydrazone alkylation methodology

L Muñoz, MP Bosch, A Guerrero

Index: Munoz, Lourdes; Bosch, Ma Pilar; Guerrero, Angel Tetrahedron Asymmetry, 2007 , vol. 18, # 5 p. 651 - 658

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Abstract

The enantioselective synthesis of both enantiomers of (Z)-1, 1, 1-trifluoro-3-methyl-4-thia-13- octadecen-2-one and (Z)-1, 1, 1-trifluoro-3-methyl-4-thia-13-hexadecen-2-one (ee⩾ 90%), potential inhibitors of the pheromone action of two major maize pests Sesamia nonagrioides and Ostrinia nubilalis, is described. The key step is based upon a stereoselective alkylation with methyl iodide using the SAMP-/RAMP-chiral auxiliary methodology, followed by ...