1399282-38-2

Upstream product

• 1399282-13-3 (R)-5-((S)-oxiran-2-yl)pyrrolidin-2-one 
• 1399282-12-2 (R)-5-((S)-1,2-dihydroxyethyl)pyrrolidin-2-one 
• 200499-53-2 (R)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidin-2-one 
• 1399282-11-1 (R)-ethyl 4-(dibenzylamino)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-2-ynoate 
• 1399282-10-0 (R)-N,N-dibenzyl-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-yn-1-amine 
• 1399282-23-5 (R)-N,N-dibenzyl-1-((S)-2,2-dimethyl-1,3-doxolan-4-yl)-3-(trimethylsilyl)prop-2-yn-1-amine 

Relevant academic research and scientific papers

Diastereoselective construction of syn-α-oxyamines via three-component α-oxyaldehyde-dibenzylamine-alkyne coupling reaction: Application in the synthesis of (+)-β-conhydrine and its analogues

A Cu(i)-catalyzed α-oxyaldehyde-dibenzylamine-alkyne coupling reaction was delineated for the construction of α-oxyamines with excellent yields and diastereoselectivity. Crystal structure analysis and theoretical calculations were also supportive of the formation of syn-α-oxyamines as the major products. Application of the methodology addresses the synthesis of (+)-β-conhydrine along with analogs having two different diversity features. A ring size variation allows construction of piperidine and pyrrolidine rings while a variation of side arm functionality is achieved by complete regioselective opening of epoxide by different organocopper ylides (Gilman reagents). A lactam-Cu(i) complexation motif is proposed which allows an intramolecular attack of ylides at the terminal epoxy carbon via the six-membered cyclic transition state. The present work features the synthesis of (+)-β-conhydrine over eight steps in 26% yield and its seven analogs in 21-28% yields.