Organic & Biomolecular Chemistry 2012-08-07

A tripeptide-like prolinamide-thiourea as an aldol reaction catalyst.

Stamatis Fotaras, Christoforos G Kokotos, George Kokotos

Index: Org. Biomol. Chem. 10(29) , 5613-9, (2012)

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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.