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A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst.
Org Biomol Chem. 2012 Aug 07; 10(29):5613-9.OB

Abstract

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.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Fotaras S
Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis 15771, Athens, Greece.
Kokotos CG
No affiliation info available
Kokotos G
No affiliation info available

MeSH

AldehydesCatalysisEthylenediaminesHydrogenIsomerismKetonesOligopeptidesProlineStereoisomerismThiourea

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

22717593

Citation

Fotaras, Stamatis, et al. "A Tripeptide-like Prolinamide-thiourea as an Aldol Reaction Catalyst." Organic & Biomolecular Chemistry, vol. 10, no. 29, 2012, pp. 5613-9.
Fotaras S, Kokotos CG, Kokotos G. A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst. Org Biomol Chem. 2012;10(29):5613-9.
Fotaras, S., Kokotos, C. G., & Kokotos, G. (2012). A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst. Organic & Biomolecular Chemistry, 10(29), 5613-9. https://doi.org/10.1039/c2ob25693b
Fotaras S, Kokotos CG, Kokotos G. A Tripeptide-like Prolinamide-thiourea as an Aldol Reaction Catalyst. Org Biomol Chem. 2012 Aug 7;10(29):5613-9. PubMed PMID: 22717593.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst. AU - Fotaras,Stamatis, AU - Kokotos,Christoforos G, AU - Kokotos,George, Y1 - 2012/06/20/ PY - 2012/6/22/entrez PY - 2012/6/22/pubmed PY - 2013/1/23/medline SP - 5613 EP - 9 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 10 IS - 29 N2 - 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. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/22717593/A_tripeptide_like_prolinamide_thiourea_as_an_aldol_reaction_catalyst_ DB - PRIME DP - Unbound Medicine ER -