Tetrahedron p. 935 - 948 (1983)
Update date:2022-08-03
Topics:
Danheiser, Rick, L.
Carini, David, J.
Fink, David M.
Basak, Ajoy
A new, regiospecific <3+2> 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.
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Doi:10.1021/ic5021737
(2014)Doi:10.1021/jo050712d
(2005)Doi:10.1016/S0040-4039(00)81323-4
(1983)Doi:10.1021/jo0509049
(2005)Doi:10.1007/s11172-020-2868-6
(2020)Doi:10.1080/00397919508015452
(1995)
