American Chemical Society
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Intramolecular Tandem Michael-Type Addition/Aldol Cyclization Induced by TiCl4−R4NX Combinations

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journal contribution
posted on 2002-08-03, 00:00 authored by Kazunari Yagi, Takayuki Turitani, Hiroshi Shinokubo, Koichiro Oshima
Treatment of formyl α,β-enones with a TiCl4−R4NX combination induces an intramolecular aldol cyclization to furnish 2-acyl-3-halocyclohexanol with three controlled consecutive stereogenic centers. The reaction of bis-α,β-enones with the combination provides cyclic diketones with high stereoselectivity via an intramolecular Michael addition reaction.