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

AuthorsMuñoz, Lourdes ; Bosch, María Pilar ; Guerrero, Ángel
β-thiotrifluoromethyl ketones
Optically active compounds
Pheromone antagonists
Issue Date19-Mar-2007
CitationTetrahedron: Asymmetry 18(5): 651-658 (2007)
AbstractThe 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 deprotection under non-racemization conditions.
Description8 pages, 1 figure.-- Printed version published on Mar 30, 2007.
Publisher version (URL)http://dx.doi.org/10.1016/j.tetasy.2007.02.022
Appears in Collections:(IQAC) Artículos
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