115522-58-2

Upstream product

• 1121-63-7 cyclohepta-3,5-dien-1-ol 
• 100-39-0 benzyl bromide 

Downstream Products

• 217025-84-8 meso-(3R,5s,7S)-5-(benzyloxy)-3,7-diacetoxycyclohept-1-ene 
• 132622-29-8 1β-hydroxy-4β-chloro-6α-(benzyloxy)-2-cycloheptene 
• 132622-31-2 1β-(p-toluenesulfonamido)-4-chloro-6α-(benzyloxy)-2-cycloheptene 
• 132622-32-3 1β-(p-toluenesulfonamido)-2β,3β-epoxy-4α-chloro-6α-(benzyloxy)-2-cycloheptene 
• 115522-45-7 1β-acetoxy-4α-(p-toluenesulfonamido)-6α-(benzyloxy)-2-cycloheptene 
• 132622-35-6 1β-((tert-butyldimethylsilyl)oxy)-4α-(p-toluenesulfonamido)-6α-(benzyloxy)-2-cycloheptene 
• 498-45-3 scopine 
• 498-46-4 pseudoscopine 
• 135-97-7 pseudotropine 
• 120-29-6 3-tropanol 
• 538-09-0 nortropine 
• 115522-45-7 Acetic acid (1R,4S,6S)-6-benzyloxy-4-(toluene-4-sulfonylamino)-cyclohept-2-enyl ester 
• 115522-46-8 Acetic acid (1R,3R,5R)-3-benzyloxy-5-(toluene-4-sulfonylamino)-cycloheptyl ester 
• 115522-46-8 Acetic acid (1S,3S,5R)-3-benzyloxy-5-(toluene-4-sulfonylamino)-cycloheptyl ester 

Relevant academic research and scientific papers

The palladium-catalyzed aerobic kinetic resolution of secondary alcohols: Reaction development, scope, and applications

The first palladium-catalyzed enantioselective oxidation of secondary alcohols has been developed, utilizing the readily available diamine (-)-sparteine as a chiral ligand and molecular oxygen as the stoichiometric oxidant. Mechanistic insights regarding the role of the base and hydrogen-bond donors have resulted in several improvements to the original system. Namely, addition of cesium carbonate and tert-butyl alcohol greatly enhances reaction rates, promoting rapid resolutions. The use of chloroform as solvent allows the use of ambient air as the terminal oxidant at 23°C, resulting in enhanced catalyst selectivity. These improved reaction conditions have permitted the successful kinetic resolution of benzylic, allylic, and cyclopropyl secondary alcohols to high enantiomeric excess with good-toexcellent selectivity factors. This catalyst system has also been applied to the desymmetrization of meso-diols, providing high yields of enantioenriched hydroxyketones.

Stereocontrolled Epoxidations of Cycloheptene Derivatives in the Palladium-Catalyzed Route to Tropane Alkaloids. Total Syntheses of Scopine and Pseudoscopine

Stereoselective total syntheses of the tropane alkaloids scopine (1) and pseudoscopine (3) have been developed via the chloroacetoxylation approach.Palladium-catalyzed 1,4-chloroacetoxylation of diene 6 afforded the key intermediate 7.Subsequent substitution of the allylic chloride by TsNH- with either retention (Pd(0) catalysis) or inversion (SN2) of configuration gave 10 and 16, respectively.The epoxy oxygen was introduced syn to the nitrogen function prior to cyclization by utilizing the syn-directive effect of the allylic sulfonamido group in the epoxidation.Cyclization of the epoxides 12 and 21, followed by replacement of the tosyl group by a methyl group and subsequent debenzylation, afforded the title compounds 1 and 3, respectively.