An enantioselective synthesis of insecticidal 4-alkynyloxazolines.
2-(2,6-Difluorophenyl)-4-phenylalkynyl oxazolines are potent insect growth regulators. An efficient and enantioselective synthesis to these compounds has been developed which relies on a (-)-sparteine mediated hydroxymethylation of the lithium dianion of propargylic amides.
Clark
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DuPont Crop Protection, Stine/Haskell Research Center, PO Box 30, Bldg 300, Newark, DE 19714, USA. david.a.clark@usa.dupont.com
Travis
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D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D018360:Crystallography, X-Ray; D020128:Inhibitory Concentration 50; D007306:Insecticides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D008925:Mites / Q000187:drug effects; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D018411:Spodoptera / Q000187:drug effects; D013237:Stereoisomerism
D000480:Alkynes; D007306:Insecticides; D010080:Oxazoles