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Enantioselective Synthesis of AG‐041R by using N ‐Heteroarenesulfonyl Cinchona Alkaloid Amides as Organocatalysts
Author(s) -
Hara Noriyuki,
Nakamura Shuichi,
Sano Masahide,
Tamura Ryota,
Funahashi Yasuhiro,
Shibata Norio
Publication year - 2012
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.201200367
Subject(s) - cinchona , enantioselective synthesis , alkaloid , cinchona alkaloids , chemistry , organocatalysis , catalysis , organic chemistry , nitrogen atom , hydrogen bond , optically active , medicinal chemistry , stereochemistry , molecule , group (periodic table)
The organocatalytic enantioselective decarboxylative addition of malonic acid half thioesters to ketimines derived from isatins by using N ‐heteroarenesulfonyl cinchona alkaloid amides afforded products with high enantioselectivity. The products could be converted into optically active AG‐041R. X‐ray crystallographic analysis revealed that the hydrogen bonding between the sulfonimide proton and the 8‐quinolyl nitrogen atom plays an important role in exerting the enantioselectivity of the reaction.