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Peptide‐Catalyzed Stereoselective Conjugate Addition Reactions of Aldehydes to Maleimide
Author(s) -
Grünenfelder Claudio E.,
Kisunzu Jessica K.,
Wennemers Helma
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.201602230
Subject(s) - maleimide , chemistry , stereoselectivity , conjugate , tripeptide , catalysis , peptide , addition reaction , stereochemistry , combinatorial chemistry , organic chemistry , biochemistry , mathematical analysis , mathematics
The tripeptide H‐ d Pro‐Pro‐Asn‐NH 2 is presented as a catalyst for asymmetric conjugate addition reactions of aldehydes to maleimide. The peptidic catalyst promotes the reaction between various aldehydes and unprotected maleimide with high stereoselectivities and yields. The obtained products were readily derivatized to the corresponding pyrrolidines, lactams, lactones, and peptide‐like compounds. 1 H NMR spectroscopic, crystallographic, and computational investigations provided insight into the conformational properties of H‐ d Pro‐Pro‐Asn‐NH 2 and revealed the importance of hydrogen bonding between the peptide and maleimide for catalyzing the stereoselective C−C bond formation.