Diastereoselective epoxidation of compound bearing a cyclohex-3-enol moiety: Application to the enantioselective synthesis of (1R)-trans-chrysanthemic acid and (1R)-cis-deltametrinic acid

A. Krief, S. Jeanmart, A. Kremer

Research output: Contribution to journalArticle

Abstract

We disclose the synthesis of enantiomeric (1S)-cis- and (1R)-cis-chrysanthemic acids precursors of S-bioallethrin and deltamethrin the most active indoor and outdoor insecticides respectively. It involves an original strategy which takes advantage of the complete stereocontrolled epoxidation of an homoallylalcohol and the synthesis in the same pot of precursors of each of the two enantiomers of cis-chrysanthemic acid, bearing functional groups possessing similar reactivity but having different structural behavior which allow their easy separation.
Original languageEnglish
Pages (from-to)1075-1079
JournalHeterocycles
Volume76
Issue number2
DOIs
Publication statusPublished - 1 Nov 2008

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NSC 153174
Bearings (structural)
Epoxidation
Enantiomers
Insecticides
Functional groups
chrysanthemic acid

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abstract = "We disclose the synthesis of enantiomeric (1S)-cis- and (1R)-cis-chrysanthemic acids precursors of S-bioallethrin and deltamethrin the most active indoor and outdoor insecticides respectively. It involves an original strategy which takes advantage of the complete stereocontrolled epoxidation of an homoallylalcohol and the synthesis in the same pot of precursors of each of the two enantiomers of cis-chrysanthemic acid, bearing functional groups possessing similar reactivity but having different structural behavior which allow their easy separation.",
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T1 - Diastereoselective epoxidation of compound bearing a cyclohex-3-enol moiety: Application to the enantioselective synthesis of (1R)-trans-chrysanthemic acid and (1R)-cis-deltametrinic acid

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AU - Jeanmart, S.

AU - Kremer, A.

PY - 2008/11/1

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N2 - We disclose the synthesis of enantiomeric (1S)-cis- and (1R)-cis-chrysanthemic acids precursors of S-bioallethrin and deltamethrin the most active indoor and outdoor insecticides respectively. It involves an original strategy which takes advantage of the complete stereocontrolled epoxidation of an homoallylalcohol and the synthesis in the same pot of precursors of each of the two enantiomers of cis-chrysanthemic acid, bearing functional groups possessing similar reactivity but having different structural behavior which allow their easy separation.

AB - We disclose the synthesis of enantiomeric (1S)-cis- and (1R)-cis-chrysanthemic acids precursors of S-bioallethrin and deltamethrin the most active indoor and outdoor insecticides respectively. It involves an original strategy which takes advantage of the complete stereocontrolled epoxidation of an homoallylalcohol and the synthesis in the same pot of precursors of each of the two enantiomers of cis-chrysanthemic acid, bearing functional groups possessing similar reactivity but having different structural behavior which allow their easy separation.

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U2 - 10.3987/COM-08-S(N)117

DO - 10.3987/COM-08-S(N)117

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