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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
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
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