453537-89-8Relevant academic research and scientific papers
1,2-dioxines as masked Cis γ-hydroxy enones and their versatility in the synthesis of highly substituted γ-lactones
Greatrex, Ben W.,Kimber, Marc C.,Taylor, Dennis K.,Fallon, Gary,Tiekink, Edward R. T.
, p. 5307 - 5314 (2002)
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.
An asymmetric synthesis of trans -fused butyrolactones from endoperoxides
Priest, Joshua,Longland, Mark. R.,Elsegood, Mark R. J.,Kimber, Marc C.
, p. 3476 - 3481 (2013/06/26)
The intermolecular addition of 1,3-dicarbonyl equivalents to endoperoxides in the presence of an organocatalyst yields trans-fused butyrolactones in high yield and enantioselectivities. This methodology expands the synthetic utility of endoperoxides and f
