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Dynamic covalent organocatalysts discovered from catalytic systems through rapid deconvolution screening.

ABSTRACT: The first example of a bifunctional organocatalyst assembled through dynamic covalent chemistry (DCC) is described. The catalyst is based on reversible imine chemistry and can catalyze the Morita-Baylis-Hillman (MBH) reaction of enones with aldehydes or N-tosyl imines. Furthermore, these dynamic catalysts were shown to be optimizable through a systemic screening approach, in which large mixtures of catalyst structures were generated, and the optimal catalyst could be directly identified by using dynamic deconvolution. This strategy allowed one-pot synthesis and in situ evaluation of several potential catalysts without the need to separate, characterize, and purify each individual structure. The systems were furthermore shown to catalyze and re-equilibrate their own formation through a previously unknown thiourea-catalyzed transimination process.

SUBMITTER: Schaufelberger F

PROVIDER: S-EPMC4557047 | biostudies-literature | 2015 Sep

REPOSITORIES: biostudies-literature

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Dynamic covalent organocatalysts discovered from catalytic systems through rapid deconvolution screening.

Schaufelberger Fredrik F Ramström Olof O

Chemistry (Weinheim an der Bergstrasse, Germany) 20150714 36

The first example of a bifunctional organocatalyst assembled through dynamic covalent chemistry (DCC) is described. The catalyst is based on reversible imine chemistry and can catalyze the Morita-Baylis-Hillman (MBH) reaction of enones with aldehydes or N-tosyl imines. Furthermore, these dynamic catalysts were shown to be optimizable through a systemic screening approach, in which large mixtures of catalyst structures were generated, and the optimal catalyst could be directly identified by using ...[more]

PMID: 26174068

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