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Stereoselective Arene‐Forming Aldol Condensation: Synthesis of Axially Chiral Aromatic Amides
Author(s) -
Fäseke Vincent C.,
Sparr Christof
Publication year - 2016
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/anie.201602689
Subject(s) - atropisomer , amide , chemistry , stereoselectivity , enantioselective synthesis , aldol condensation , condensation , amine gas treating , reactivity (psychology) , organic chemistry , ring (chemistry) , combinatorial chemistry , aldol reaction , catalysis , medicine , physics , alternative medicine , pathology , thermodynamics
The increasing awareness of the importance of amide atropisomers prompts the development of novel strategies for their selective preparation. Described herein is a method for the enantioselective synthesis of atropisomeric aromatic amides by an amine‐catalyzed arene‐forming aldol condensation. The high reactivity of the glyoxylic amide substrates enables a remarkably efficient construction of a new aromatic ring, which proceeds within minutes at ambient temperature to afford products with excellent stereoselectivity. The high rotational barriers of the reduced products highlight the utility of this stable, spatially organized chiral scaffold.