Issue 23, 2006

Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones

Abstract

This article describes the synthesis of a library of structurally diverse bifunctional organocatalysts bearing both a quasi-Lewis acidic (thio)urea moiety and a Brønsted basic tertiary amine group. Sequential modification of the modular catalyst structure and subsequent screening of the compounds in the alcoholytic dynamic kinetic resolution (DKR) of azlactones revealed valuable structure–activity relationships. In particular, a “hit-structure” was identified which provides e.g.N-benzoyl-tert-leucine allyl ester in an excellent enantiomeric excess of 95%.

Graphical abstract: Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones

Supplementary files

Article information

Article type
Paper
Submitted
30 May 2006
Accepted
29 Sep 2006
First published
01 Nov 2006

Org. Biomol. Chem., 2006,4, 4319-4330

Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones

A. Berkessel, S. Mukherjee, T. N. Müller, F. Cleemann, K. Roland, M. Brandenburg, Jörg-M. Neudörfl and J. Lex, Org. Biomol. Chem., 2006, 4, 4319 DOI: 10.1039/B607574F

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