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

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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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-01, Vol.50 (56), p.7447-7450
Main Authors: Ceban, Victor, Putaj, Piotr, Meazza, Marta, Pitak, Mateusz B, Coles, Simon J, Vesely, Jan, Rios, Ramon
Format: Article
Language:English
Subjects:
Activation
Carbonates
Catalysis
Direct reduction
Lewis base
Metalorganic compounds
Synthesis
X rays
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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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc00728j