127299-56-3

Upstream product

• 627-27-0 homoalylic alcohol 
• 127299-55-2 (3R,4R)-3,4-bis(benzyloxy)pyrrolidine-2,5-dione 
• 321566-90-9 (3R,4R)-3,4-bis(benzyloxy)-1-(4-methoxybenzyl)-pyrrolidine-2,5-dione 
• 138794-81-7 (2R,3R)-2,3-bis(benzyloxy)tartaric acid 
• 97506-01-9 (3R,4R)-3,4-bis(benzyloxy)-3,4-dihydro-2,5-furandione 
• 77312-71-1 diethyl (2R,3R)-2,3-bis(benzyloxy)butane-1,4-dioate 

Downstream Products

• 1401240-63-8 (1R,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-8a-hydroxy-7-methylhexahydroindolizin-3(5H)-one 
• 1401240-65-0 (1R,2R,7R,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-8a-hydroxy-7-methylhexahydroindolizin-3(5H)-one 
• 1401240-85-4 (1S,2R,7S,8aR)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one 
• 1401240-86-5 (1S,2R,7S,8aS)-1,2-bis(benzyloxy)-8,8-difluoro-7-methylhexahydro-indolizin-3(5H)-one 
• 1401240-87-6 (1S,2S,3R,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine 
• 1401240-89-8 (1S,2S,3S,7S,8aR)-1,2-bis(benzyloxy)-3-ethyl-8,8-difluoro-7-methyloctahydroindolizine 
• 1401240-88-7 (1S,2S,3R,7S,8aR)-1,2-bis(benzyloxy)-3-butyl-8,8-difluoro-7-methyloctahydroindolizine 
• 1401240-91-2 (S)-2-(benzyloxy)-8-butyl-7-methyl-6,7-dihydroindolizin-3(5H)-one 
• 1401240-92-3 (S)-2-(benzyloxy)-8-isopropyl-7-methyl-6,7-dihydroindolizin-3(5H)-one 
• 1401240-48-9 (3R,4R,5R)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one 
• 1401240-50-3 (3R,4R,5S)-3,4-bis(benzyloxy)-1-(but-3-enyl)-5-(difluoro(phenylthio)methyl)-5-hydroxypyrrolidin-2-one 
• 127379-94-6 (1S,2R,8aR)-1,2-Bis-benzyloxy-hexahydro-indolizine-3,7-dione 
• 127299-59-6 (1S,2R,8aS)-1,2-Bis-benzyloxy-hexahydro-indolizine-3,7-dione 
• 127299-62-1 (1S,2R)-1,2-Bis-benzyloxy-7-hydroxy-hexahydro-indolizin-3-one 

Relevant academic research and scientific papers

Asymmetric synthesis of gem-difluoromethylenated dihydroxypyrrolizidines and indolizidines

An asymmetric synthesis of gem-difluoromethylenated dihydroxypyrrolizidines and indolizidines is described. The fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 (1) to chiral imides was achieved in satisfactory yields to provide mixtures of syn- and anti-isomers 6-9 with moderate to good diastereoselectivities. Reductive cleavage of the phenylsulfanyl group followed by intramolecular radical cyclization of the syn-isomers 6-9 occurred under refluxing conditions to afford the corresponding gem-difluoromethylenated 1-azabicyclic compounds 10-13 in moderate yields as a separable mixture of cis- and trans-isomers. The cis-isomers of compounds 10 and 12 and trans-13 were readily transformed to gem-difluoromethylenated dihydroxypyrrolizidines 20 and 27 and indolizidine 28, respectively, by reductive cleavage of the hydroxyl group and organometallic addition followed by hydrogenolysis.

Acyliminium cyclization of several chiral N-alkenylsuccinimide derivatives

The acyliminium intermediate derived from (3R,4R)-N-(3-butenyl)-3,4-bis(benzyloxy)succinimide cyclized to give (8aS)- and (8aR)-hexahydro-3(2H)-indolidinone derivatives. On the other hand, those derived from N-3-hexenyl derivatives afforded (8aS)-hexahydr