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Issue 7, 2014
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Stereoselective allylboration of imines and indoles under mild conditions. An in situ E/Z isomerization of imines by allylboroxines

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Abstract

Direct allylboration of various acyclic and cyclic aldimine, ketimine and indole substrates was performed using allylboronic acids. The reaction proceeds with very high anti-stereoselectivity for both E and Z imines. The allylboroxines formed by dehydration of allylboronic acids have a dual effect: promoting E/Z isomerization of aldimines and triggering the allylation by efficient electron withdrawal from the imine substrate.

Graphical abstract: Stereoselective allylboration of imines and indoles under mild conditions. An in situ E/Z isomerization of imines by allylboroxines

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The article was received on 07 Feb 2014, accepted on 03 Mar 2014 and first published on 04 Mar 2014


Article type: Edge Article
DOI: 10.1039/C4SC00415A
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Citation: Chem. Sci., 2014,5, 2732-2738
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    Stereoselective allylboration of imines and indoles under mild conditions. An in situ E/Z isomerization of imines by allylboroxines

    R. Alam, A. Das, G. Huang, L. Eriksson, F. Himo and K. J. Szabó, Chem. Sci., 2014, 5, 2732
    DOI: 10.1039/C4SC00415A

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