Reactions of five- and/or six-membered-ring ketones 1–5 possessing an ω-halogenoalkyl group and α′,β′-unsaturated ester function at the α-position with diorganocuprates afforded the oxapropellane compounds 20–24 in a one-pot, three-step procedure via 1,4-addition followed by intramolecular aldol condensation and O-alkylation. Similar reaction of α,α′-disubstituted cyclopentanone 6 afforded bicyclic products 28 and 29.
C. Fang, K. Suganuma, H. Suemune and K. Sakai, J. Chem. Soc., Perkin Trans. 1, 1991, 1549 DOI: 10.1039/P19910001549
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