A tripeptide-like prolinamide-thiourea catalyst with (S)-proline, (1S,2S)-diphenylethylenediamine and (S)-di-tert-butyl aspartate as building blocks provides the products of the reaction between ketones and aromatic aldehydes in high to quantitative yields and high stereoselectivities (up to 99 : 1 dr and 99% ee). Both the chiral centers of the diamine unit are essential, while the thiourea hydrogen originating from the amine and the amide hydrogen play a predominant role for the catalyst efficiency.
This article is part of themed collection Organocatalysis of Royal Society of Chemistry (RSC)
Type
Text (Journal article)
Scientific Coordinator
Κόκοτος, Γεώργιος-Ισίδωρος
Project Notes
Πράξη: Σύνθεση νέων χειρόμορφων οργανοκαταλυτών (ακινητοποιημένων ή μη) και μελέτη της καταλυτικής δράσης τους σε ασύμμετρους οργανικούς μετασχηματισμούς