Please use this identifier to cite or link to this item: https://doi.org/10.1021/jo020700h
Title: A novel synthesis of functionalized tetrahydrofurans by an Oxa-Michael/Michael cyclization of γ-hydroxyenones
Authors: Greatrex, B.W.
Kimber, M.C.
Taylor, D.K.
Tiekink, E.R.T. 
Issue Date: 30-May-2003
Citation: Greatrex, B.W., Kimber, M.C., Taylor, D.K., Tiekink, E.R.T. (2003-05-30). A novel synthesis of functionalized tetrahydrofurans by an Oxa-Michael/Michael cyclization of γ-hydroxyenones. Journal of Organic Chemistry 68 (11) : 4239-4246. ScholarBank@NUS Repository. https://doi.org/10.1021/jo020700h
Abstract: An approach to highly functionalized tetrahydrofuran derivatives based upon a novel Oxa-Michael/ Michael dimerization of cis-γ-hydroxyenones is presented. The reaction begins with either 1,2-dioxines or trans-γ-hydroxyenones and proceeds by addition of one molecule of trans-γ-hydroxyenone to another molecule of cis- or trans-γ-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 γ-hydroxyenone is tolerated; however, for 4-substituted γ-hydroxyenones, selectivity issues arise due to the possibility of heterochiral or homochiral dimerizations. The major products were those with all contiguous groups trans.
Source Title: Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/92986
ISSN: 00223263
DOI: 10.1021/jo020700h
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