Camphor-derived alcohols as chiral auxiliaries for asymmetric Pauson-Khand bicyclizations. Enantioselective synthesis of α-methoxyenones

Xavier Verdaguer, Albert Moyano, Miquel A. Pericàs, Antoni Riera, Andrew E. Greene, Joan F. Piniella, Angel Alvarez-Larena

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51 Citations (Scopus)

Abstract

The intramolecular Pauson-Khand reaction of enol and ynol ethers of Oppolzer's camphor-derived neopentyloxy alcohols is described. Bicyclic products are obtained in yields of up to 65% and with diastereoselectivities as high as 94:6 under very mild reaction conditions. The absolute configurations of the major stereoisomers obtained when (1R, 2S, 3R, 4S)-3-neopentyloxy-1,7,7-trimethylbicyclo- [2.2.1]heptan-2-ol is used as a chiral auxiliary are rationalized on the basis of the theoretically predicted preferential conformations of model precursors. A simple procedure for obtaining auxiliary-free, enantiopure bicyclic α-methoxyenones is also presented. © 1992.
Original languageEnglish
Pages (from-to)305-310
JournalJournal of Organometallic Chemistry
Volume433
Issue number3
DOIs
Publication statusPublished - 28 Jul 1992

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