138371-93-4

Upstream product

• 138371-92-3 N-ethoxycarbonyl-2-phenacylpiperidine 
• 138371-91-2 N-ethoxycarbonyl-2-ethoxypiperidine 
• 33485-71-1 2-oxopiperidine-1-carboxylic acid ethyl ester 
• 13735-81-4 1-styrenyloxytrimethylsilane 

Downstream Products

• 70561-76-1 (±)-allosedamine 
• 497-88-1 sedamine 

Relevant academic research and scientific papers

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed amidoalkylation of silylenolethers. Stereocontrolled syntheses of (+/-)-sedamine and (+/-)-norsedamine

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) catalyzed addition of 1-trimethylsilyloxy-1-phenylethene to N-ethoxycarbonyl- and N-tert-butoxycarbonyl-2-ethoxypiperidines (3a and 3b, respectively) afforded the corresponding ketocarbamates 4a and 4b, in excellent yields. Stereoselective conversion to (±)-norsedamine (7) and (±)-sedamine (8) is described.