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https://hdl.handle.net/2440/18011
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Type: | Journal article |
Title: | A novel synthesis of functionalized tetrahydrofurans by an oxa-Michael/Michael cyclization of g-hydroxyenones |
Author: | Greatrex, B. Kimber, M. Taylor, D. Tiekink, E. |
Citation: | Journal of Organic Chemistry, 2003; 68(11):4239-4246 |
Publisher: | Amer Chemical Soc |
Issue Date: | 2003 |
ISSN: | 0022-3263 1520-6904 |
Statement of Responsibility: | Ben W. Greatrex, Marc C. Kimber, Dennis K. Taylor, and Edward R. T. Tiekink |
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. |
Description: | Copyright © 2003 American Chemical Society |
DOI: | 10.1021/jo020700h |
Published version: | http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/2003/68/i11/abs/jo020700h.html |
Appears in Collections: | Aurora harvest 2 Chemistry publications |
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