223906-11-4

Upstream product

• 94426-72-9 2-(2-(benzyloxy)ethyl)oxirane 
• 1066-54-2 trimethylsilylacetylene 
• 100-39-0 benzyl bromide 
• 70388-33-9 4-benzyloxybut-1-ene 

Downstream Products

• 556005-17-5 6-benzyloxy-4-methanesulfonyloxy-1-trimethylsilyl-1-hexyne 
• 556005-20-0 cis-4-amino-6-benzyloxy-1-trimethylsilyl-1-hexene 
• 556005-19-7 cis-4-azido-6-benzyloxy-1-trimethylsilyl-1-hexene 
• 556005-18-6 4-azido-6-benzyloxy-1-trimethylsilyl-1-hexyne 
• 556005-24-4 cis-4-benzylidenamino-6-benzyloxy-1-trimethylsilyl-1-hexene 
• 556005-25-5 cis-4-(N-benzyl)amino-6-benzyloxy-1-trimethylsilyl-1-hexene 
• 556005-29-9 {Benzyl-[(Z)-1-(2-benzyloxy-ethyl)-4-trimethylsilanyl-but-3-enyl]-amino}-phenyl-acetonitrile 

Relevant academic research and scientific papers

Remarkable catalytic activity of Me3Ga in the alkylation of hetero- substituted epoxides with alkynyllithiums

Regio- and stereoselective ring-opening reaction of hetero-substituted epoxides with alkynyllithiums can be catalyzed by Me3Ga with remarkable efficiency at 0-20°C via pentacoordinate chelate-type complex.

Experimental and quantum-mechanical investigation of the vinylsilane-iminium ion cyclization

A vinylsilane-ketiminium ion cyclization involving iminium species derived from amines 6 and 7 was investigated experimentally as a possible approach to some biologically interesting 1-azaspirocycles. However, even under conditions of microwave irradiatio

Pentacoordinate organoaluminum chemistry: Catalytic efficiency of Me3Al in the epoxide cleavage with alkynyllithiums

A new and highly effective catalytic method for epoxide alkynylations has been developed that involves the chelation-controlled alkylation of heterosubstituted epoxides with Me3Al via pentacoordinate organoaluminum complexes by taking advantage of the exceedingly high affinity of aluminum to oxygen. For example, reaction of epoxy ether, (1-benzyloxy)-3-butene oxide (1), in toluene with PhC?CLi under the influence of catalytic Me3Al (10 mol%) proceeded smoothly at 0 °C for 5 h to furnish the alkynylation product, 1-(benzyloxy)-6-phenylhex-5-yn-3-ol, in 76% yield [cf. 3% without Me3Al catalyst; 78% with stoichiometric Me3Al under similar conditions]. This represents the first catalytic procedure for the amphiphilic alkylation of epoxides. The participation of pentacoordinate Me3Al complexes of epoxy ethers of type 1 is emphasized by comparing the reactivity with the corresponding simple epoxide, 5-phenyl-1-pentene oxide, which was not susceptible to nucleophile attack of PhC?CLi with catalytic Me3Al under similar conditions. The pentacoordinate complex formation of Me3Al with epoxy ether 1 is characterized by low-temperature 13C and 27Al NMR spectroscopy. This approach is also applicable to the selective alkynylation of tosyl aziridines with adjacent ether functionality, which provides a promising method for amino alcohol synthesis.