A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst.
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.
Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis 15771, Athens, Greece.
Stamatis
S
Fotaras
Christoforos G
CG
Kokotos
George
G
Kokotos
D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D005029:Ethylenediamines / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry; D007536:Isomerism; D007659:Ketones / Q000737:chemistry; D009842:Oligopeptides / Q000737:chemistry*; D011392:Proline / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism; D013890:Thiourea / Q000737:chemistry*
D000447:Aldehydes; D005029:Ethylenediamines; D007659:Ketones; D009842:Oligopeptides; C518332:diphenylethylenediamine; D006859:Hydrogen; D011392:Proline; D013890:Thiourea; C056291:prolinamide