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Issue 18, 2013
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Synergistic effects within a C2-symmetric organocatalyst: the potential formation of a chiral catalytic pocket

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Abstract

This study describes the synthesis of five novel C2-symmetric organocatalysts that facilitate the on-water asymmetric aldol reaction at low catalyst loading (1 mol%) without the use of additives. Each catalyst is composed of two diprolinamide units joined by a symmetric alkyl bridging group allowing for systematic modulation of catalytic site proximity. Typically, catalysts in this manuscript which bear the catalytic units in close proximity gave the best reaction outcomes in terms of conversion (up to >99%), diastereomeric ratio (4/96, syn/anti) and enantiomeric excess (up to 97%). This effect has been attributed to the assembly of a chiral pocket, facilitated by hydrogen bonding at the oil-in-water interface.

Graphical abstract: Synergistic effects within a C2-symmetric organocatalyst: the potential formation of a chiral catalytic pocket

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Publication details

The article was received on 20 Nov 2012, accepted on 15 Feb 2013 and first published on 18 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB27250H
Citation: Org. Biomol. Chem., 2013,11, 2951-2960
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    Synergistic effects within a C2-symmetric organocatalyst: the potential formation of a chiral catalytic pocket

    J. P. Delaney, H. L. Brozinski and L. C. Henderson, Org. Biomol. Chem., 2013, 11, 2951
    DOI: 10.1039/C3OB27250H

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