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Michael Addition Reactions of Highly Basic Enolates for the Formation of 2‐(Tosylamino)Dihydrochalcones
Author(s) -
Zheng Jing,
Meng Zhongrong,
Lu Doudou,
Zhao Dongxin,
Chen Qinfang,
Yang Weiran
Publication year - 2019
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.201900514
Subject(s) - chemistry , tetramethylammonium , ketone , yield (engineering) , fluoride , reaction conditions , tetramethylammonium hydroxide , organic chemistry , combinatorial chemistry , catalysis , ion , inorganic chemistry , materials science , metallurgy
A protocol for the reaction of ketone or ester enolates with aza‐ o ‐quinodimethanes (aza‐o‐QMs) formed in situ is reported via a 1,4‐elimination in the presence of tetramethylammonium fluoride (TMAF). The reaction partners were reacted to provide a wide variety of substituted 2‐(tosylamino)dihydrochalcones in 45–97% yield in a single reaction sequence in one pot under mild condition. Additionally, various 2‐(tosylamino)dihydrochalcones could be easily converted to form diverse heterocycles.