6874-86-8

Upstream product

• 498-95-3 (S)-nipecotic acid 
• 37675-18-6 (S)-(+)-nipecotic acid ethyl ester 
• 191599-51-6 ethyl (S)-1-[(tert-butoxy)carbonyl]piperidine-3-carboxylate 
• 616866-58-1 (R)-4-[(S)-5-methylene-1-(toluene-4-sulfonyl)piperidin-2-yl]pent-2-enoic acid ethyl ester 
• 616866-56-9 N-{1-[2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-4-(hydroxymethyl)pent-4-enyl}-4-methylbenzenesulfonamide 
• 616866-52-5 2(S)-[2-(tert-butyl-dimethyl-silanyloxy)-1(S)-methyl-ethyl]-5-methylene-1-(toluene-4-sulfonyl)-piperidine 
• 616866-50-3 2(S)-[2-(tert-butyl-dimethyl-silanyloxy)-1(S)-methyl-ethyl]-N-(p-toluenesulfonyl)-aziridine 
• 616866-65-0 (S)-2-[(S)-5-methylene-1-(toluene-4-sulfonyl)piperidin-2-yl]propan-1-ol 
• 616866-46-7 (2R,3S)-N-(p-toluenesulfonyl)-3-methylaspartic acid dimethyl ester 
• 616866-48-9 (1R,2S)-N-(3-hydroxy-1-hydroxymethyl-2-methyl-propyl)-4-methylbenzenesulfonamide 
• 616866-42-3 2(S)-[N-(p-toluenesulfonyl)-aziridin-2(S)-yl]-propan-1-ol 
• 616866-40-1 (1R,9S)-1-methyl-7-methyleneoctahydro-4H-quinolizin-4-one 
• 60161-30-0 4-(furan-3-yl)-1-methyl-7-methyleneoctahydro-2H-quinolizine 

Relevant academic research and scientific papers

One-Pot Reductive Allylation of Amides by Using a Combination of Titanium Hydride and an Allylzinc Reagent: Application to a Total Synthesis of (-)-Castoramine

A one-pot direct reductive allylation protocol has been developed for the synthesis of secondary amines by using titanium hydride and an allylzinc reagent. This protocol is applicable to a broad range of substrates, including acyclic amides, benzamides, α,β-unsaturated amides, and lactams. The stereochemical outcome obtained from the reaction with crotylzinc reagent suggested that the allylation reaction proceeds through a six-membered cyclic transition state. A total synthesis of (-)-castoramine was accomplished by following this protocol for the highly stereoselective construction of contiguous stereocenters.

Development of a flexible approach to Nuphar alkaloids via two enantiospecific piperidine-forming reactions

(Chemical Equation Presented). In this paper we describe the stereoselective synthesis of functionalized lactam 7 via two enantiospecific piperidine-forming techniques and its employment in a general synthetic approach to Nuphar alkaloids. Specifically, the formation of piperidine 18 by formal [3 + 3] cycloaddition and stepwise annelation processes is described; the latter technique was found to be significantly more efficient than the Pd-catalyzed TMM addition process. Finally, exploitation of the exocyclic alkene installed in the piperidine-forming reaction in the transformation of 18 to (-)-deoxynupharidine ((-)-2), (-)-castoramine ((-)-3), and (-)-nupharolutine ((-)-4) via intermediate lactam 7 is delineated.