Publication: Stereoselective Synthesis of gem-Difluoromethylenated Linear Azatriquinanes
Issued Date
2018-01-17
Resource Type
ISSN
10990690
1434193X
1434193X
Other identifier(s)
2-s2.0-85040718541
Rights
Mahidol University
Rights Holder(s)
SCOPUS
Bibliographic Citation
European Journal of Organic Chemistry. Vol.2018, No.2 (2018), 160-169
Suggested Citation
Chonticha Masusai, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr Stereoselective Synthesis of gem-Difluoromethylenated Linear Azatriquinanes. European Journal of Organic Chemistry. Vol.2018, No.2 (2018), 160-169. doi:10.1002/ejoc.201701415 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/45513
Research Projects
Organizational Units
Authors
Journal Issue
Thesis
Title
Stereoselective Synthesis of gem-Difluoromethylenated Linear Azatriquinanes
Other Contributor(s)
Abstract
© 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim The stereoselective synthesis of gem-difluoromethylenated linear azatriquinanes is described herein. The fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 (1), exploited as a gem-difluoromethylene (-CF2-) building block, to chiral phthalimide 2 provided the corresponding gem-difluoromethylenated adduct 3 in high yield as a diastereomeric mixture. The stereoselective intramolecular radical cyclization of 3 furnished chiral linear azatriquinanes 4, the hydroxy group of which subsequently underwent nucleophilic substitution by organosilanes to provide 5 with high stereoselectivity. Treatment of 5 with Grignard reagents or a reducing agent provided a collection of chiral gem-difluoromethylenated linear azatriquinanes 6–8.