Publication: Fluoride-catalyzed addition of PhSCF2SiMe3 to N-substituted cyclic imides followed by radical cyclization: General synthetic strategy of gem-difluoromethylenated 1-azabicyclic compounds
Issued Date
2009-05-15
Resource Type
ISSN
00223263
Other identifier(s)
2-s2.0-65949102530
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
Journal of Organic Chemistry. Vol.74, No.10 (2009), 3798-3805
Suggested Citation
Teerawut Bootwicha, Duanghathai Panichakul, Chutima Kuhakarn, Samran Prabpai, Palangpon Kongsaeree, Patoomratana Tuchinda, Vichai Reutrakul, Manat Pohmakotr Fluoride-catalyzed addition of PhSCF2SiMe3 to N-substituted cyclic imides followed by radical cyclization: General synthetic strategy of gem-difluoromethylenated 1-azabicyclic compounds. Journal of Organic Chemistry. Vol.74, No.10 (2009), 3798-3805. doi:10.1021/jo802794u Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/27418
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
Fluoride-catalyzed addition of PhSCF2SiMe3 to N-substituted cyclic imides followed by radical cyclization: General synthetic strategy of gem-difluoromethylenated 1-azabicyclic compounds
Other Contributor(s)
Abstract
(Chemical Equation Presented) PhSCF2SiMe3 (1) was found, for the first time, to undergo fluoride-catalyzed nucleophilic difluoro(phenylsulfanyl)methylation reaction to cyclic imides 2, affording the corresponding adducts 3 in moderate to good yields. Reductive cleavage of the phenylsulfanyl group of N-alkylated adducts 3 with Bu3SnH/AIBN yielded gem-difluoromethylated products 4. Under the same reduction conditions, N-alkenylated and N-alkynylated adducts 3 afforded the corresponding gem-difluoromethylenated 1-azabicyclic compounds 5 and 6 with trans stereoselectivity. These compounds were employed as precursors for preparing substituted gem-difluoromethylenated pyrrolizidinones and indolizidinones 7 and 8 by treatment with Et3SiH/BF3·OEt2, and compounds 9 and 10 by nucleophilic displacement of the hydroxyl group, using organosilanes in the presence of BF3·OEt2. The synthesis of highly substituted gem-difluoromethylenated pyrrolizidines 13 and 14 was also demonstrated. © 2009 American Chemical Society.