1427520-29-3

Basic information

• Product Name: ((3R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
• Synonyms: ((3R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone
• CAS NO: 1427520-29-3
• Molecular Weight: 575.844
• Mol File: 1427520-29-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: ((3R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone(CAS DataBase Reference)
• NIST Chemistry Reference: ((3R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone(1427520-29-3)
• EPA Substance Registry System: ((3R,6R)-6-(((tert-butyldimethylsilyl)oxy)methyl)-3-methyl-5-phenyl-1-tosyl-1,2,3,6-tetrahydropyridin-4-yl)(phenyl)methanone(1427520-29-3)

Safety Data

• Hazardous Substances Data: 1427520-29-3(Hazardous Substances Data)

Upstream product

• 1427519-98-9 (3S,4S)-4-(N-allyl-4-methylphenylsulfonamido)-5-((tertbutyldimethylsilyl)oxy)-1,3-diphenylpent-1-yn-3-yl cyclopropanecarboxylate 
• 1383950-54-6 N-((2S,3S)-1-((tert-butyldimethylsilyl)oxy)-3-hydroxy-3,5-diphenylpent-4-yn-2-yl)-4-methylbenzenesulfonamide 

Relevant articles and documents

Gold-catalyzed cycloisomerization of 1,7-enyne esters to structurally diverse cis -1,2,3,6-tetrahydropyridin-4-yl ketones

A synthetic method that relies on gold(I)-catalyzed cycloisomerization of 1,7-enyne esters to prepare highly functionalized cis-1,2,3,6-tetrahydropyridin- 4-yl ketone derivatives in good to excellent yields and as a single regio-, diastereo-, and enantiomer is described. By taking advantage of the distinctive differences in the electronic and steric properties between an NHC (NHC = N-heterocyclic carbene) and phosphine ligand in the respective gold(I) complexes, a divergence in product selectivity was observed. In the presence of [PhCNAuIPr]+SbF6- (IPr = 1,3-bis(2,6- diisopropylphenyl)imidazol-2-ylidine) as the catalyst, tandem 1,3-acyloxy migration/6-exo-trig cyclization/1,5-acyl migration of the substrate was found to selectively occur to give the δ-diketone-substituted 1,2,3,6-tetrahydropyridine adduct. In contrast, reactions with the gold(I) phosphine complex [MeCNAu(JohnPhos)]+SbF6- (JohnPhos = (1,1′-biphenyl-2-yl)-di-tert-butylphosphine) as the catalyst was discovered to result in preferential 1,3-acyloxy migration/6-exo-trig cyclization/hydrolysis of the 1,7-enyne ester and formation of the cis-1,2,3,6-tetrahydropyridin-4-yl ketone derivative. The utility of this piperidine forming strategy as a synthetic tool that makes use of 1,7-enyne esters was exemplified by its application to the synthesis of an enantiopure analogue of the bioactive 2,3,4,4a,5,9b-hexahydroindeno[1,2-c]pyridine family of compounds.