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Synthesis of 2‐Cyclohexenone‐2‐carboxylate and 4‐Chloro‐2‐cyclohexenone‐2‐carboxylate Derivatives by Cyclization of Alkyne‐Tethered 1,3‐Ketoesters
Author(s) -
Kaewsri Wilailak,
Norseeda Krissada,
Ruengsangtongkul Sureeporn,
Chaisan Nattawadee,
Thongsornkleeb Charnsak,
Tummatorn Jumreang,
Ruchirawat Somsak
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700510
Subject(s) - chemistry , cyclohexenone , alkyne , carboxylate , decarboxylation , reagent , combinatorial chemistry , catalysis , organic chemistry , medicinal chemistry
A method for the TfOH‐promoted (Tf=trifluoromethanesulfonyl) cyclization of alkyne‐tethered 1,3‐ketoesters to afford 2‐cyclohexenone‐2‐carboxylate derivatives has been developed. The procedure requires no transition‐metal reagent or catalyst and is practical to conduct under mild conditions. 2‐Cyclohexenone‐2‐carboxylate derivatives were obtained in moderate to good yields without any evidence of decarboxylation. In addition, the approach can be easily adapted as a one‐pot sequential cyclization/chlorination protocol that selectively provides access to 4‐chloro‐2‐cyclohexenone‐2‐carboxylate derivatives in moderate to good yields.