A Novel Synthesis of Functionalized Tetrahydrofurans by an Oxa-Michael/Michael Cyclization of γ-Hydroxyenones
- 1 May 2003
- journal article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (11) , 4239-4246
- https://doi.org/10.1021/jo020700h
Abstract
An approach to highly functionalized tetrahydrofuran derivatives based upon a novel Oxa-Michael/Michael dimerization of cis-gamma-hydroxyenones is presented. The reaction begins with either 1,2-dioxines or trans-gamma-hydroxyenones and proceeds by addition of one molecule of trans-gamma-hydroxyenone to another molecule of cis- or trans-gamma-hydroxyenone catalyzed by an alkoxide or hydroxide base. Subsequent intramolecular Michael addition of the keto-enolate gives the observed tetrahydrofurans. Substitution at both the 2- and 4-positions of the gamma-hydroxyenone is tolerated; however, for 4-substituted gamma-hydroxyenones, selectivity issues arise due to the possibility of heterochiral or homochiral dimerizations. The major products were those with all contiguous groups trans.Keywords
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