96845-72-6Relevant articles and documents
Synthesis of eight-membered lactones: Intermolecular [6+2] cyclization of amphoteric molecules with siloxy alkynes
Zhao, Wanxiang,Wang, Zhaobin,Sun, Jianwei
supporting information; experimental part, p. 6209 - 6213 (2012/07/17)
That's about the size of it: The title molecules react with siloxy alkynes in the presence of a Bronsted acid to deliver medium-sized lactones through a [6+2] cyclization (see scheme; TIPS=triisopropylsilyl). This process is the first intermolecular synthesis of such lactones and involves a sequence of several selective ring-opening/ring-closing events. Copyright
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.
Silver-catalyzed [2 + 2] cycloadditions of siloxy alkynes
Sweis, Randy F.,Schramm, Michael P.,Kozmin, Sergey A.
, p. 7442 - 7443 (2007/10/03)
We have described the first [2 + 2] cycloadditions of siloxy alkynes with a range of unsaturated carbonyl compounds. The reactions are efficiently promoted by substoichiometric amount of silver trifluoromethanesulfonimide and display excellent regio- and diastereoselectivity combined with a broad substrate scope. Our studies have established unambiguously the stepwise mechanism of this process and provided evidence for a novel role of silver in the catalytic cycle of the reaction, which involves silver-based complexation and activation of siloxy alkyne toward the subsequent 1,4-addition. Copyright
