214116-40-2Relevant academic research and scientific papers
Hetero [4 + 2] cycloadditions of (trialkylsilyl)vinylketenes. Synthesis of α,β-unsaturated δ-valerolactones and -lactams
Bennett, Dawn M.,Okamoto, Iwao,Danheiser, Rick L.
, p. 641 - 644 (1999)
(Matrix presented) Hetero Diels-Alder reactions of (trialkylsilyl)vinylketenes (TAS-vinylketenes) with carbonyl and imino dienophiles are described. TAS-vinylketenes participate as electron-rich dienes in [4 + 2] cycloadditions with diethyl ketomalonate t
A benzannulation strategy for the synthesis of phenols and heteroaromatic compounds based on the reaction of (trialkylsilyl)vinylketenes with lithium ynolates
Austin, Wesley F.,Zhang, Yongjun,Danheiser, Rick L.
, p. 915 - 925 (2008/09/16)
(Trialkylsilyl)vinylketenes react with lithium ynolates to generate 3-(oxido)dienylketenes, which undergo rapid 6π-electrocyclization. The ultimate products of this benzannulation are highly substituted resorcinol monosilyl ethers, which are formed via a [1,3] carbon to oxygen silyl?group shift. Further transformations of the benzannulation products are described providing efficient access to ortho-benzoquinones and benzofuran, benzoxepine, and benzoxocine ring systems.
(Trialkylsilyl)vinylketenes: Synthesis and application as diene components in Diels-Alder cycloadditions
Loebach, Jennifer L.,Bennett, Dawn M.,Danheiser, Rick L.
, p. 8380 - 8389 (2007/10/03)
New strategies for the synthesis of (trialkylsilyl)vinylketenes ('TAS- vinylketenes') are described based on the photochemical Wolff rearrangement of α'-silyl-α'-diazo-α,β-unsaturated ketones and the 4π electrocyclic ring opening of cyclobutenones. These remarkably robust vinylketenes undergo highly regioselective [4 + 2] cycloadditions with reactive olefinic and acetylenic dienophiles to produce highly substituted cyclohexenones and phenols in which the ketene carbonyl dominates in controlling the regiochemical course of the reaction. The stereochemical course of these cycloadditions follows the Alder endo rule, as illustrated in the reaction of nitropropene with TAS-vinylketene 22.
