86186-40-5Relevant academic research and scientific papers
SCOPE AND STEREOCHEMICAL COURSE OF THE (TRIMETHYLSILYL)CYCLOPENTENE ANNULATION
Danheiser, Rick, L.,Carini, David, J.,Fink, David M.,Basak, Ajoy
, p. 935 - 948 (1983)
A new, regiospecific annulation approach to highly substituted 5-membered carbocycles has been developed.The "TMS-cyclopentene annulation" involves the reaction of (trimethylsilyl)allenes with electrondeficient alkenes and alkynes in the presence of titanium tetrachloride to afford, in a single step, a functionalized and highly substituted TMS-cyclopentene derivative.Annulations employing α, β-unsaturated ketones proceed stereoselectively via suprafacial addition to the enone.Some useful transformations of the annulation products are also described; for example, treatment with K2CO3-methanol or HF in acetonitrile effects isomerization and desilylation yielding α, β-unsaturated ketones.
