153681-99-3

Upstream product

• 119461-44-8 ((Z)-(S)-1-Methyl-4-trimethylsilanyl-but-3-enyl)-[1-phenyl-meth-(E)-ylidene]-amine 
• 100-46-9 benzylamine 
• 119461-42-6 (S)-N-(p-toluenesulfonyl)-4-amino-1-Z-(trimethylsilyl)-1-pentene 
• 98-88-4 benzoyl chloride 
• 119461-43-7 (S)-4-amino-1-(trimethylsilyl)-1-pentyne 
• 100-52-7 benzaldehyde 
• 100-39-0 benzyl bromide 
• 81939-73-3 (2S)-2-hydroxypent-4-yne 
• 153681-98-2 N-Benzyl-4-methyl-N-((Z)-(S)-1-methyl-4-trimethylsilanyl-but-3-enyl)-benzenesulfonamide 

Downstream Products

• 119461-49-3 rac-trans-N-benzyl-6-methyl-2-phenyl-1,2,5,6-tetrahydropyridine 
• 119461-47-1 [Benzyl-((Z)-(S)-1-methyl-4-trimethylsilanyl-but-3-enyl)-amino]-phenyl-acetonitrile 
• 40240-12-8 1-benzyl-1,2,3,6-tetrahydropyridine 
• 153682-03-2 (S)-1-Benzyl-2-methyl-1,2,3,6-tetrahydro-pyridine 
• 109838-90-6 N-benzyl-(E)-4-(trimethylsilyl)-3-buten-1-ylamine 
• 3197-42-0 (S)-2-methylpiperidine 
• 88034-71-3 (+)-(S)-2-methylpiperidinyl-(R)-2-methoxy-2-phenyl-3,3,3-trifluoropropanamide 
• 153682-00-9 Benzyl-((Z)-(S)-1-methyl-4-trimethylsilanyl-but-3-enyl)-trimethylsilanylmethyl-amine 

Relevant academic research and scientific papers

Rapid access to trans-2,6-disubstituted piperidines: Expedient total syntheses of (-)-solenopsin A and (+)-epi-dihydropinidine

Expedient syntheses of (-)-solenopsin A and (+)-epi-dihydropinidine are reported, the key step in both being the one-pot multicomponent aza-silyl-Prins condensation reaction to yield a trans dihydropyridine. Georg Thieme Verlag Stuttgart.

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.

Preparation of enantioenriched tetrahydropyridines by iminium ion-vinylsilane cyclizations

Tetrahydropyridines can be prepared from (S)-amino acids in high enantiomeric purity as outlined in equation 1.