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Organocatalytic Enantioselective Decarboxylative Reaction of Malonic Acid Half Thioesters with Cyclic N ‐Sulfonyl Ketimines by Using N ‐Heteroarenesulfonyl Cinchona Alkaloid Amides
Author(s) -
Nakamura Shuichi,
Sano Masahide,
Toda Ayaka,
Nakane Daisuke,
Masuda Hideki
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201406270
Subject(s) - enantioselective synthesis , cinchona , chemistry , malonic acid , decarboxylation , sulfonyl , enantiomer , organocatalysis , organic chemistry , cinchona alkaloids , nucleophile , catalysis , alkyl
The organocatalytic enantioselective decarboxylative Mannich reaction of malonic acid half thioesters (MAHTs) with cyclic N ‐sulfonyl ketimines by using N ‐heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. Both enantiomers of the products could be obtained by using pseudoenantiomeric chiral catalysts. The reaction proceeds through a nucleophilic addition of the MAHTs to the ketimines prior to decarboxylation.