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

Publication at Faculty of Science |
2014

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.