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Synthesis 1988; 1988(10): 823-826
DOI: 10.1055/s-1988-27722
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Improved Wittig Condensation of Trifluoromethyl Ketones with Non Stabilized Phosphorus Ylides: Application to the Synthesis of Precursors of Insect Juvenile Hormone III Trifluoroanalogues

Francisco Camps* , Francisco-José Sanchez, Angel Messeguer
  • *Department of Biological Organic Chemistry (C.I.D.), C.S.I.C., J. Girona 18, E-08034 Barcelona, Spain
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Publication Date:
12 September 2002 (online)

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An improved methodology for Wittig condensation of trifluoromethyl ketones with non-stabilized phosphorus ylides, which takes place under smooth and homogeneous reaction conditions, is reported. By this procedure trifluoromethyl alkenes 3a-c are obtained in almost quantitative yields and with a high stereochemical control. The use of 3b and 3c as building blocks for the preparation of the corresponding trifluoro esters 7a and 7b, which are potential insect growth regulators, is also described.

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