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Stereoselective Nucleophilic Addition of PhSCF 2 SiMe 3 to Chiral Cyclic Nitrones: Asymmetric Synthesis of gem ‐Difluoromethylenated Polyhydroxypyrrolizidines and ‐indolizidines
Author(s) -
Korvorapun Korkit,
Soorukram Darunee,
Kuhakarn Chutima,
Tuchinda Patoomratana,
Reutrakul Vichai,
Pohmakotr Manat
Publication year - 2015
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201403023
Subject(s) - nucleophilic addition , chemistry , adduct , stereoselectivity , nucleophile , chiral auxiliary , fluoride , stereochemistry , enantioselective synthesis , organic chemistry , medicinal chemistry , catalysis , inorganic chemistry
Fluoride‐catalyzed nucleophilic addition of a difluoro(phenylsulfanyl)methyl group (“PhSCF 2 ”) generated from PhSCF 2 SiMe 3 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.