88034-71-3

Upstream product

• 20445-33-4 (R)-methoxytrifluoromethylphenylacetyl chloride 
• 3197-42-0 (S)-2-methylpiperidine 
• 119461-42-6 (S)-N-(p-toluenesulfonyl)-4-amino-1-Z-(trimethylsilyl)-1-pentene 
• 153682-03-2 (S)-1-Benzyl-2-methyl-1,2,3,6-tetrahydro-pyridine 
• 153682-00-9 Benzyl-((Z)-(S)-1-methyl-4-trimethylsilanyl-but-3-enyl)-trimethylsilanylmethyl-amine 
• 109-05-7 2-Methylpiperidin 
• 153681-98-2 N-Benzyl-4-methyl-N-((Z)-(S)-1-methyl-4-trimethylsilanyl-but-3-enyl)-benzenesulfonamide 
• 153681-99-3 (S)-N-benzyl-N-(Z)-(1-methyl-4-trimethylsilylbut-3-enyl)amine 
• 39637-99-5 (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride 

Relevant academic research and scientific papers

An Oxidative Mannich Cyclization Methodology for the Stereocontrolled Synthesis of Highly Functionalized Piperidines

Studies focusing on the development and application of a new oxidative methodology for promoting Mannich cyclizations have been conducted. The general features of these processes were explored with selected α-silylamino and α-silylamido allyl- and vinylsilanes. Representative conditions for affecting conversion of the α-silylamine and -amide functionalities into intermediate N-alkyl and N-acyliminium cations involve either 9,10-dicyanoanthracene SET-sensitized photooxidation or ceric ammonium or tetra-n-butylammonium nitrate oxidations. The applicability of these procedures for promoting Mannich cyclizations was first demonstrated by the preparation of methylidenepi- peridines and -hydroazepines. Further studies have led to observations which show that Mannich cyclizations of stereochemically labeled α-silylamino vinylsilanes proceed to furnish tetrahydro- pyridines. Also, unlike their amine analogues, α-silylamido (E)-vinylsilanes undergo cyclization to produce tetrahydropyridines with retention of absolute and relative stereochemistry. The differences are due to the fact that N-acyliminium cations serve as intermediates in reactions of the α-silylamide systems. Moreover, the oxidation procedure is ideally suited for intermediate N-acyliminium cation generation in stereocontrolled reactions of α-silylamido allylsilanes. Finally, the preparative utility of the new cyclization method, when used in conjunction with an α-amino acid based strategy for substrate generation, was demonstrated by applications in concise routes for the synthesis of the aza-sugars, (-)-1-deoxymannojirimycin and (+)-l-deoxyallonojirimycin.

Conformational analysis of chiral hindered amides

The static and dynamic structures of the amide derivatives of racemic and (R)-(+)-2-methoxy-2-phenyl-3,3,3-trifluoropropanoic acid (MTPA with diisopropyl amine (1), meso-2,6-dimethylpiperidine (2), (R)-(-)- and (S)-(+)-2-methylpiperidine (3 and 4, respect