Please use this identifier to cite or link to this item:
|Title:||1,2-dioxines as masked Cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones|
|Source:||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|
Show full item record
Files in This Item:
There are no files associated with this item.
checked on Feb 15, 2018
WEB OF SCIENCETM
checked on Jan 30, 2018
checked on Feb 19, 2018
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.