426827-19-2

Upstream product

• 408351-32-6 [2(1S,3E),2S]-2-[[1-tert-butyl-4-(trimethylsilanyl)but-3-enyl]amino]-2-phenylethanol 
• 882-33-7 diphenyldisulfane 
• 426827-15-8 [4(1S),5S]-4-(1-tert-butyl-4-trimethylsilanylbut-3-enyl)-5-phenylmorpholin-2-one 

Downstream Products

• 426827-23-8 (4S,6S,9aS)-6-tert-butyl-4-phenyl-3,4,7,9a-tetrahydro-6H-pyrido[2,1-c][1,4]oxazin-1-one 

Relevant academic research and scientific papers

The intriguing reactivity of functionalized β-amino alcohols with glyoxal: Application to a new expedient enantioselective synthesis of trans-6-alkylpipecolic acids

New β-amino alcohols possessing a vinylsilane moiety were reacted with glyoxal to produce lactones that were transformed in three steps in enantiopure pipecolic acid derivatives. The key step was a totally diastereoselective ene-iminium cyclization, whose mechanism can be viewed as a direct cyclization of the vinylsilane moiety onto the iminium ion. The reactivity of two β-amino alcohols having an allylsilane terminator was also examined. Their difference of reactivity toward glyoxal can be ascribed to the intervention of a carbocation, which presents a behavior that differs according to the position of the trimethylsilyl group.