Premium
Gold(I)‐Catalyzed Tandem Cycloisomerization and Fluorination of 1,3(4)‐Enyne Esters with NFSI: One‐Pot Assembly of 5‐Fluoro‐ Cyclopentenones
Author(s) -
Chen Xianxiao,
Zhou Yuanyuan,
Hong Mei,
Ling Yuan,
Yin Dongliang,
Wang Shifa,
Zhang Xiaoxiang,
Rao Weidong
Publication year - 2018
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201800701
Subject(s) - cycloisomerization , enyne , chemistry , combinatorial chemistry , stereocenter , tandem , catalysis , electrophile , electrophilic fluorination , fluorine , cascade reaction , stereochemistry , organic chemistry , enantioselective synthesis , composite material , materials science
An efficient synthetic approach for the synthesis of 5‐fluoro‐cyclopentenones containing a fluorine‐substituted carbon stereocenter that relies on gold(I)‐catalyzed cycloisomerization and fluorination sequence of 1,3(4)‐enyne esters with N‐fluorbenzensulfonimide (NFSI) is described. This tandem transformation exhibited a broad substrate scope and excellent functional group compatibility, providing a novel protocol for rapid assembly 5‐fluoro‐cyclopentenones in good to excellent yields under mild reaction conditions. The mechanistic studies revealed that the transformation involves a gold‐catalyzed cycloisomerization and electrophilic fluorination cascade to give the 5‐fluoro‐cyclopentenones.