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

Issued Date

2015-01-01

Resource Type

Article

ISSN

1861471X
18614728

DOI

10.1002/asia.201403023

Other identifier(s)

2-s2.0-84925590476

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Chemistry - An Asian Journal. Vol.10, No.4 (2015), 948-968

Suggested Citation

Korkit Korvorapun, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Vichai Reutrakul, Manat Pohmakotr Stereoselective nucleophilic addition of PhSCF<inf>2</inf>SiMe<inf>3</inf> to chiral cyclic nitrones: Asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines. Chemistry - An Asian Journal. Vol.10, No.4 (2015), 948-968. doi:10.1002/asia.201403023 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/35763

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Title

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

Author(s)

Korkit Korvorapun
 Darunee Soorukram
 Chutima Kuhakarn
 Patoomratana Tuchinda
 Vichai Reutrakul
 Manat Pohmakotr

Other Contributor(s)

Mahidol University

Abstract

© 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.

Keyword(s)

Chemistry

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/35763

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Scopus 2011-2015