4372-10-5Relevant academic research and scientific papers
Asymmetric synthesis of novel spirocycles via a chiral phosphoric acid catalyzed desymmetrization
Kelley, Amber M.,Minerali, Eni,Wilent, Jennifer E.,Chambers, Nicholas J.,Stingley, Kyla J.,Wilson, G. Tyler,Petersen, Kimberly S.
, p. 1262 - 1264 (2019/04/10)
A straightforward method for the asymmetric preparation of novel lactone and lactam spirocycles is described. An initial desymmetrization via a chiral Br?nsted acid yields enantioenriched lactones which readily undergo a second cyclization to give the des
Manganese(III)-Mediated Spirodilactonization
Fristad, William E.,Hershberger, Susan S.
, p. 1026 - 1031 (2007/10/02)
Manganese(III) oxidation of malonic acid in the presence of alkenes results in the formation of spiro-fused lactones, 2,7-dioxaspirononane-1,6-diones.Terminal alkenes produce a mixture of the three possible diastereomers.The stereochemistry of the diastereomeric spirodilactones was determined by NMR and corroborated by the intensity of the coupled IR carbonyl stretching frequencies. 1,1,6,6-Tetrasubstituted 1,5-hexadienes give in one step tricyclic dilactones.Mechanistic and synthetic aspects of this reaction are discussed.
