19872-53-8Relevant academic research and scientific papers
Rh-Mediated Cyclopentane Construction Can Compete with β-Hydride Elimination: Synthesis of (+/-)-Tochuinyl Acetate
Taber, Douglass F.,Hennessy, Michael J.,Louey, James P.
, p. 436 - 441 (2007/10/02)
Rhodium(II) carboxylate catalyzed C-H insertion to form a cyclopentane is shown to compete effectively with β-hydride elimination, except when the β-hydrogen is ternary.Cyclization of diazo ester 27 gives 28, which is converted in three steps to (+/-)-toc
Dienophilic Properties of Phenyl Vinyl Sulfone and trans-1-(Phenylsulfonyl)-2-(trimethylsilyl)ethylene. Their Utilization as Synthons for Ethylene, 1-Alkenes, Acetylene, and Monosubstituted Alkynes in the Construction of Functionalized Six-Membered Rings via ? Cycloaddition Meth.
Carr, Richard V. C.,Williams, Richard V.,Paquette, Leo A.
, p. 4976 - 4986 (2007/10/02)
Useful procedures for effecting the indirect capture of ethylene, acetylene, 1-alkenes, and monosubstituted alkynes in Diels-Alder cycloadditions have been developed.In the first sequence, phenyl vinyl sulfone is shown to enter into ? reactions as a moderately reactive dienophile and to do so with very good regioselectivity.The resulting adducts can be directly desulfonated or alkylated prior to such reduction.A wide range of functional groups can be appended in this fashion at a specific locus within the newly formed six-membered ring.When the analogous chemistry is applied to trans-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene (2), adducts result which undergo ready fluoride ion induced elimination with efficient introduction of a double bond.The use of 2 and its d2 derivative is highlighted by the synthesis of several functionalized dibenzobarrelenes.
