138907-13-8Relevant academic research and scientific papers
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.
Stereo- and regioselective metal salt-catalyzed alkynylation of 1,2-epoxides
Chini,Crotti,Favero,Macchia
, p. 6617 - 6620 (2007/10/02)
A simple, efficient, stereoselective, and highly regioselective method for the synthesis of β-hydroxyacetylenes by the direct opening of 1,2-epoxides with lithium acetylides in anhydrous THF, in the presence of metal salts, is described. This new method a
