Please use this identifier to cite or link to this item: https://doi.org/10.1021/jo0200421
Title: 1,2-dioxines as masked Cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones
Authors: Greatrex, B.W.
Kimber, M.C.
Taylor, D.K.
Fallon, G.
Tiekink, E.R.T. 
Issue Date: 26-Jul-2002
Citation: Greatrex, B.W., Kimber, M.C., Taylor, D.K., Fallon, G., Tiekink, E.R.T. (2002-07-26). 1,2-dioxines as masked Cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones. Journal of Organic Chemistry 67 (15) : 5307-5314. ScholarBank@NUS Repository. https://doi.org/10.1021/jo0200421
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.
Source Title: Journal of Organic Chemistry
URI: http://scholarbank.nus.edu.sg/handle/10635/92896
ISSN: 00223263
DOI: 10.1021/jo0200421
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