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Stereoselective Synthesis of gem ‐Difluoromethylenated Linear Azatriquinanes
Author(s) -
Masusai Chonticha,
Soorukram Darunee,
Kuhakarn Chutima,
Reutrakul Vichai,
Pohmakotr Manat
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701415
Subject(s) - chemistry , stereoselectivity , diastereomer , intramolecular force , nucleophilic substitution , nucleophilic addition , phthalimide , stereochemistry , enantioselective synthesis , nucleophile , medicinal chemistry , organic chemistry , catalysis
The stereoselective synthesis of gem ‐difluoromethylenated linear azatriquinanes is described herein. The fluoride‐catalyzed nucleophilic addition of PhSCF 2 SiMe 3 ( 1 ), exploited as a gem ‐difluoromethylene (‐CF 2 ‐) building block, to chiral phthalimide 2 provided the corresponding gem ‐difluoromethylenated adduct 3 in high yield as a diastereomeric mixture. The stereoselective intramolecular radical cyclization of 3 furnished chiral linear azatriquinanes 4 , the hydroxy group of which subsequently underwent nucleophilic substitution by organosilanes to provide 5 with high stereoselectivity. Treatment of 5 with Grignard reagents or a reducing agent provided a collection of chiral gem ‐difluoromethylenated linear azatriquinanes 6 – 8 .