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Deprotonative Generation of Cyclohexynes from Cyclic Enol Triflates Using Aluminate Bases
Author(s) -
Hioki Yuto,
Yukioka Taro,
Okano Kentaro,
Mori Atsunori
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.201800205
Subject(s) - enol , chemistry , aluminate , nitrone , cycloaddition , lithium (medication) , base (topology) , organic chemistry , catalysis , metallurgy , materials science , cement , medicine , mathematical analysis , mathematics , endocrinology
Deprotonative generation of cyclohexynes was achieved by treatment of the corresponding enol triflates with lithium triisobutyl(2,2,6,6‐tetramethylpiperidino)aluminate as a base. Six‐membered enol triflates involving an ester and a cyano group were converted to the corresponding cyclohexynes at 60 °C. The reaction conditions were applied to [3+2] cycloaddition with a nitrone to form the isoxazoline.