Stereoselective nucleophilic addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to chiral cyclic nitrones: Asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines

Stereoselective nucleophilic addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to chiral cyclic nitrones: Asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines

© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Fluoride-catalyzed nucleophilic addition of a difluoro(phenylsulfanyl)methyl group ("PhSCF2") generated from PhSCF2SiMe3 to nitrones was accomplished in satisfactory yields. High diastereoselectivities were observed with chiral polyo...

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Bibliographic Details
Main Authors: Korkit Korvorapun, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Vichai Reutrakul, Manat Pohmakotr
Other Authors: Mahidol University
Format: Article
Published: 2018
Subjects:
Chemistry
Online Access:https://repository.li.mahidol.ac.th/handle/123456789/35763
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Institution: Mahidol University
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Summary:© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. Fluoride-catalyzed nucleophilic addition of a difluoro(phenylsulfanyl)methyl group ("PhSCF2") generated from PhSCF2SiMe3 to nitrones was accomplished in satisfactory yields. High diastereoselectivities were observed with chiral polyoxygenated cyclic nitrones to provide the corresponding adducts, which were further manipulated to afford gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines.

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