34501-28-5Relevant articles and documents
Stereoselective reduction of α,β-epoxy ketones with sodium borohydride in the presence of calcium chloride or lanthanum chloride. A practical preparation of erythro-α,β-epoxy alcohols
Taniguchi,Fujii,Oshima,Utimoto
, p. 679 - 686 (1995)
erythro-Epoxy alcohols were prepared with high stereoselectivity by NaBH4 reduction of the corresponding α,β-epoxy ketones in the presence of calcium chloride or lanthanum chloride regardless of the substituents on the epoxide ring.
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.
Divergent stereoselectivity in the reduction of α,β-epoxy ketones using hydridosilicates
Hojo, Makoto,Fujii, Atsuko,Murakami, Chikara,Aihara, Hidenori,Hosomi, Akira
, p. 571 - 574 (2007/10/02)
α,β-Epoxy ketones are reduced by trimethoxysilane in the presence of a catalytic amount of lithium melboxide to yield the corresponding alcohols. This reaction system reveals divergent selectivity depending on the solvent; both anti-selectivity and syn-se
