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Issue 2, 2015
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Structure–activity relationship studies of cyclopropenimines as enantioselective Brønsted base catalysts

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Abstract

We recently demonstrated that chiral cyclopropenimines are viable Brønsted base catalysts in enantioselective Michael and Mannich reactions. Herein, we describe a series of structure–activity relationship studies that provide an enhanced understanding of the effectiveness of certain cyclopropenimines as enantioselective Brønsted base catalysts. These studies underscore the crucial importance of dicyclohexylamino substituents in mediating both reaction rate and enantioselectivity. In addition, an unusual catalyst CH⋯O interaction, which provides both ground state and transition state organization, is discussed. Cyclopropenimine stability studies have led to the identification of new catalysts with greatly improved stability. Finally, additional demonstrations of substrate scope and current limitations are provided herein.

Graphical abstract: Structure–activity relationship studies of cyclopropenimines as enantioselective Brønsted base catalysts

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Publication details

The article was received on 07 Aug 2014, accepted on 19 Nov 2014 and first published on 19 Dec 2014


Article type: Edge Article
DOI: 10.1039/C4SC02402H
Citation: Chem. Sci., 2015,6, 1537-1547
  • Open access: Creative Commons BY license
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    Structure–activity relationship studies of cyclopropenimines as enantioselective Brønsted base catalysts

    J. S. Bandar, A. Barthelme, A. Y. Mazori and T. H. Lambert, Chem. Sci., 2015, 6, 1537
    DOI: 10.1039/C4SC02402H

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