77548-25-5Relevant academic research and scientific papers
One-pot Annulation of Enones with Lithiated Allyl Phenyl Sulfone
Dong, Zemin,Pyne, Stephen G.,Skelton, Brian W.,White, Allan H.
, p. 103 - 104 (1997)
A one-pot method of converting five and six membered cyclic enones to their respective bicyclo[2.2.1]heptanones and bicyclo[2.2.2]octanones, respectively, and acyclic enones to cyclohex-3-enols is reported.
REGIOSELECTIVITY IN THE REACTION OF CYCLOPENTENONES WITH CARBAIONS OF PHENYL ALLYL SULFIDE, SULFOXIDE, AND SULFONE
Vasil'eva, L. L.,Mel'nikova, V. I.,Gainullina, E. T.,Pivnitskii, K. K.
, p. 835 - 843 (2007/10/02)
The condensation of allylic carbanion of phenyl allyl sulfide, sulfoxide, and sulfone with 2-cyclopenten-1-one takes place by mechanisms of 1,2-addition and regioselective and nonregioselective 1,4-addition respectively.The reaction of phenyl allyl sulfone anion gives the 1,4-γ-adduct preferentially in the case of the lithium counterion and the 1,4-α-adduct with the potassium counterion.The 1,4-γ-addition of the phenyl allyl sulfoxide anion to 2-cyclopenten-1-one is characterized by full stereoselectivity, which also remains during the condensations of the phenyl1-vinylhexyl sulfoxide anion and 4-(1-methyl-1-phenylethoxy)-2-cyclopenten-1-one (prostaglandin synthons).
