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Issue 56, 2014
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Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita–Baylis–Hillman carbonates

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Abstract

An expedited method has been developed for the diastereoselective synthesis of highly functionalized alkyl-azaarene systems with good yields and high diastereoselectivities (>15 : 1 dr). The methodology includes a synergistic catalysis event involving organometallic (10 mol% AgOAc) activation of an alkyl azaarene and Lewis base (10 mol% DABCO) activation of a Morita–Baylis–Hillman carbonate. The structure and relative configuration of a representative product were confirmed by X-ray analysis.

Graphical abstract: Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita–Baylis–Hillman carbonates

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Supplementary files

Article information


Submitted
29 Jan 2014
Accepted
16 May 2014
First published
20 May 2014

Chem. Commun., 2014,50, 7447-7450
Article type
Communication
Author version available

Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita–Baylis–Hillman carbonates

V. Ceban, P. Putaj, M. Meazza, M. B. Pitak, S. J. Coles, J. Vesely and R. Rios, Chem. Commun., 2014, 50, 7447
DOI: 10.1039/C4CC00728J

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