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Issue 10, 2017
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A complementary pair of enantioselective switchable organocatalysts

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Abstract

A pair of enantioselective switchable bifunctional catalysts are shown to promote a range of conjugate addition reactions in up to 95 : 5 e.r. and 95% conversion. Each catalyst can be switched OFF using conditions that switch the other catalyst ON. Catalyst ON : OFF ratios of up to 98 : 2 and 1 : 99 were achieved, with a ratio of reaction rates of up to 16 : 1 between the ON and OFF states, maintained over complete ON–OFF–ON and OFF–ON–OFF cycles. However, simultaneous operation of the catalyst pair in the same reaction vessel, which in principle could allow product handedness to be switched by simple EZ isomerisation of the catalyst pair, was unsuccessful. In this first generation complementary pair of enantioselective switchable organocatalysts, the OFF state of one catalyst inhibits the ON state of the other.

Graphical abstract: A complementary pair of enantioselective switchable organocatalysts

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Publication details

The article was received on 01 Jun 2017, accepted on 22 Aug 2017 and first published on 23 Aug 2017


Article type: Edge Article
DOI: 10.1039/C7SC02462B
Citation: Chem. Sci., 2017,8, 7077-7081
  • Open access: Creative Commons BY license
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    A complementary pair of enantioselective switchable organocatalysts

    G. De Bo, D. A. Leigh, C. T. McTernan and S. Wang, Chem. Sci., 2017, 8, 7077
    DOI: 10.1039/C7SC02462B

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