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Issue 23, 2006
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Structural optimization of thiourea-based bifunctional organocatalysts for the highly enantioselective dynamic kinetic resolution of azlactones

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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

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Publication details

The article was received on 30 May 2006, accepted on 29 Sep 2006 and first published on 01 Nov 2006


Article type: Paper
DOI: 10.1039/B607574F
Citation: Org. Biomol. Chem., 2006,4, 4319-4330
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    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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