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Thioamide‐Substituted Cinchona Alkaloids as Efficient Organocatalysts for Asymmetric Decarboxylative Reactions of MAHOs
Author(s) -
Singjunla Yuttapong,
Pigeaux Morgane,
Laporte Romain,
Baudoux Jérôme,
Rouden Jacques
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700870
Subject(s) - thioamide , chemistry , cinchona alkaloids , cinchonidine , cinchona , protonation , organic chemistry , organocatalysis , malonic acid , enantioselective synthesis , mannich reaction , catalysis , ion
A new class of thioamide‐substituted cinchona derivatives is reported. A convergent and practical approach was developed to insert the thioamide functional group onto the cinchonidine from readily available dithioesters. These organocatalysts were effective in asymmetric decarboxylative Mannich and protonation reactions of α‐amido‐substituted malonic acid half oxyesters (MAHOs), affording α,β‐ and α‐amino acid derivatives, respectively, in good yields and stereoselectivities.