Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita-Baylis-Hillman carbonatesElectronic supplementary information (ESI) available: Experimental procedures and spectroscopic data. CCDC 978247. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c4cc00728j

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...

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Main Authors: Ceban, Victor, Putaj, Piotr, Meazza, Marta, Pitak, Mateusz B, Coles, Simon J, Vesely, Jan, Rios, Ramon
Format: Article
Language:English
Online Access:Get full text
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Summary: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. 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).
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc00728j