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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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Article information


Submitted
07 Feb 2014
Accepted
03 Mar 2014
First published
04 Mar 2014

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

Chem. Sci., 2014,5, 2732-2738
Article type
Edge Article
Author version available

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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