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Title: Asymmetric synthesis of gem-difluoromethylenated dihydroxypyrrolizidines and indolizidines
Authors: Watcharaporn Thaharn
Teerawut Bootwicha
Darunee Soorukram
Chutima Kuhakarn
Samran Prabpai
Palangpon Kongsaeree
Patoomratana Tuchinda
Vichai Reutrakul
Manat Pohmakotr
Mahidol University
Keywords: Chemistry
Issue Date: 5-Oct-2012
Citation: Journal of Organic Chemistry. Vol.77, No.19 (2012), 8465-8479
Abstract: An asymmetric synthesis of gem-difluoromethylenated dihydroxypyrrolizidines and indolizidines is described. The fluoride-catalyzed nucleophilic addition of PhSCF 2 SiMe 3 (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. © 2012 American Chemical Society.
ISSN: 15206904
Appears in Collections:Scopus 2011-2015

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