Gold(I)‐Catalyzed Tandem Cycloisomerization and Fluorination of 1,3(4)‐Enyne Esters with NFSI: One‐Pot Assembly of 5‐Fluoro‐ Cyclopentenones | Zendy

Chen Xianxiao | Zendy; Zhou Yuanyuan | Zendy; Hong Mei | Zendy; Ling Yuan | Zendy; Yin Dongliang | Zendy; Wang Shifa | Zendy; Zhang Xiaoxiang | Zendy; Rao Weidong | Zendy

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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.

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