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https://hdl.handle.net/2440/4549
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Type: | Journal article |
Title: | 1,2-dioxines as masked cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones |
Other Titles: | 1,2-dioxines as masked cis gamma-hydroxy enones and their versatility in the synthesis of highly substituted gamma-lactones |
Author: | Greatrex, B. Kimber, M. Taylor, D. Fallon, G. Tiekink, E. |
Citation: | Journal of Organic Chemistry, 2002; 67(15):5307-5314 |
Publisher: | Amer Chemical Soc |
Issue Date: | 2002 |
ISSN: | 0022-3263 1520-6904 |
Abstract: | Addition of highly stabilized ester nucleophiles to 1,2-dioxines affords good to high yields of γ-lactones with high diastereoselectivity. Heterolytic or homolytic cleavage of the 1,2-dioxines under appropriate conditions generates the key reactive cis γ-hydroxy enones, which ultimately afford the observed γ-lactones. Diastereoselectivity is installed as a result of anti 1,4-addition by the ester enolate to the cis enones followed by intramolecular cyclization. The reaction is tolerant of a range of substitution patterns on the 1,2-dioxine while a broad range of esters are also accommodated. In addition to the synthesis of racemic γ-lactones, highly enantioenriched γ-lactones can also be synthesized when chiral cobalt(II) catalysts are employed for the initial homolytic ring-opening of the 1,2-dioxine. |
Description: | Copyright © 2002 American Chemical Society |
DOI: | 10.1021/jo0200421 |
Published version: | http://pubs.acs.org/cgi-bin/abstract.cgi/joceah/2002/67/i15/abs/jo0200421.html |
Appears in Collections: | Aurora harvest 6 Chemistry publications |
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