189504-80-1Relevant academic research and scientific papers
NbCl5 mediated deprotection of methoxy methyl ether
Yadav,Ganganna,Bhunia, Dinesh C.,Srihari
experimental part, p. 4318 - 4320 (2009/10/26)
An efficient cleavage of methoxy methyl ether using NbCl5 is described. This protocol works efficiently with MOM ethers of alkyl, allyl, propargyl, benzyl alcohol and phenol derivatives. MOM esters are also found to be effectively cleaved under the present conditions.
Substituent effects on the regiochemical and stereochemical course of the nussbaumer-frater variation of the prins cyclization
Bennett, Chad E.,Figueroa, Ruth,Hart, David J.,Yang, Dexi
, p. 119 - 128 (2007/10/03)
Eleven vinylogous carbonates were examined in the Nussbaumer-Frater variation of the Prins cyclization to provide 2,3,4,6-tetrasubstituted tetrahydropyrans. Results indicate that substrate olefin geometry is a more reliable control element than preset sub
An alkyne hydrosilylation-oxidation strategy for the selective installation of oxygen functionality
Trost, Barry M.,Ball, Zachary T.,Laemmerhold, Kai M.
, p. 10028 - 10038 (2007/10/03)
Alkynes bearing propargylic, homopropargylic, and bishomopropargylic hydroxyl groups are shown to serve as precursors for ketone or α-hydroxy ketone functionality. The approach hinges on the intermediacy of vinylsilanes created through regioselective hydrosilylation catalyzed by the complex [Cp*Ru(MeCN)3]-PF6. Several oxidative pathways of linear and cyclic vinylsilanes are studied, and the possibility of diastereoselective epoxidation of cyclic vinylsilanes is demonstrated. The sequences constitute the equivalent of stereoselective aldol, homo-aldol, and bishomo-aldol type processes. The method is applied to a short synthesis of the piperidine alkaloid, spectaline.
