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Organocatalytic Enantioselective Conjugate Addition of Malonic Acid Half Thioesters to Coumarin‐3‐carboxylic Acids Using N ‐Heteroarenesulfonyl Cinchona Alkaloid Amides
Author(s) -
Nakamura Shuichi,
Toda Ayaka,
Sano Masahide,
Hatanaka Tsubasa,
Funahashi Yasuhiro
Publication year - 2016
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.201600040
Subject(s) - chemistry , enantioselective synthesis , cinchona , malonic acid , coumarin , conjugate , organic chemistry , organocatalysis , yield (engineering) , cinchona alkaloids , alkaloid , carboxylic acid , catalysis , mathematical analysis , materials science , mathematics , metallurgy
We disclose herein an efficient enantioselective conjugate addition reaction between coumarin‐3‐carboxylic acids and malonic acid half thioesters (MAHTs). The reaction was catalyzed by N ‐heteroarenesulfonyl Cinchona alkaloid amides to afford double‐decarboxylative conjugate addition products in good yield with high enantioselectivity. The reaction of various coumarin‐3‐carboxylic acids with MAHTs gave products in high yield with high enantioselectivity.