Stereoselective nucleophilic addition of PhSCF2 SiMe3 to chiral cyclic nitrones: asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines

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

doi:10.1002/asia.201403023

Stereoselective nucleophilic addition of PhSCF2 SiMe3 to chiral cyclic nitrones: asymmetric synthesis of gem-difluoromethylenated polyhydroxypyrrolizidines and -indolizidines

Chem Asian J. 2015 Apr;10(4):948-68. doi: 10.1002/asia.201403023. Epub 2014 Nov 21.

Authors

Korkit Korvorapun¹, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Vichai Reutrakul, Manat Pohmakotr

Affiliation

¹ Center of Excellence for Innovation in Chemistry (PERCH-CIC) and Department of Chemistry, Faculty of Science, Mahidol University, Rama VI Road, Bangkok 10400 (Thailand).

PMID: 25418141
DOI: 10.1002/asia.201403023

Abstract

Fluoride-catalyzed nucleophilic addition of a difluoro(phenylsulfanyl)methyl group ("PhSCF2 ") generated from PhSCF2 SiMe3 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.

Keywords: cyclization; fluorine; indolizidine; pyrrolizidine; radical reactions.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Indolizidines / chemical synthesis*
Molecular Structure
Nitrogen Oxides / chemistry*

Substances

Indolizidines
Nitrogen Oxides
nitrones