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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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Supplementary files

Article information


Submitted
01 Jun 2017
Accepted
22 Aug 2017
First published
23 Aug 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 7077-7081
Article type
Edge Article

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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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