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|Title:||1,2-dioxines as masked Cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones|
|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|
|Appears in Collections:||Staff Publications|
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