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Enantioselective Synthesis of Atropisomeric Amides by Dynamic Resolution: Thermodynamic Control with a Proline‐Derived Diamine Resolving Agent
Author(s) -
Clayden Jonathan P.,
Lai Lai Wah
Publication year - 1999
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19990903)38:17<2556::aid-anie2556>3.0.co;2-q
Subject(s) - enantioselective synthesis , diastereomer , diamine , hydrolysis , chemistry , amide , yield (engineering) , proline , combinatorial chemistry , organic chemistry , amino acid , materials science , catalysis , biochemistry , metallurgy
By exploiting the thermal instability about the Ar–CO axis at high temperature, atropisomeric amides can be dynamically resolved to provide material with up to 96.5 % ee in 70–80 % overall yield from racemic starting material. The amides are coupled with a diamine resolving agent and equilibrated to single diastereoisomers. Hydrolysis returns enantiomerically enriched amide (see reaction scheme).