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Issue 29, 2012
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A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst

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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.

Graphical abstract: A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst

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Publication details

The article was received on 08 Apr 2012, accepted on 30 May 2012 and first published on 31 May 2012


Article type: Paper
DOI: 10.1039/C2OB25693B
Citation: Org. Biomol. Chem., 2012,10, 5613-5619
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    A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst

    S. Fotaras, C. G. Kokotos and G. Kokotos, Org. Biomol. Chem., 2012, 10, 5613
    DOI: 10.1039/C2OB25693B

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