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Stereoselective Difluoromethylenation Using Me 3 SiCF 2 SPh: Synthesis of Chiral 2,4‐Disubstituted 3,3‐Difluoropyrrolidines
Author(s) -
Li Ya,
Hu Jinbo
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200604783
Subject(s) - synthon , stereoselectivity , nucleophile , intramolecular force , chemistry , nucleophilic addition , radical cyclization , ion , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis
A radical synthon : Nucleophilic (phenylthio)difluoromethylation of ( R )‐ N ‐( tert ‐butylsulfinyl)imines with 1 , a difluoromethylene radical anion equivalent, afforded the corresponding products in good yields and with high diastereoselectivity (d.r.≥98:2). The resulting PhSCF 2 ‐containing sulfinamides can be further transformed into chiral 2,4‐ trans ‐disubstituted 3,3‐difluoropyrrolidines through an intramolecular radical cyclization methodology.