Dual catalysis in enantioselective oxidopyrylium-based [5 + 2] cycloadditions.

J Am Chem Soc

Department of Chemistry & Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA.

Published: September 2011

A new method for effecting catalytic enantioselective intramolecular [5 + 2] cycloadditions based on oxidopyrylium intermediates is reported. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental evidence points to a new type of cooperative catalysis with each species being necessary to generate a reactive pyrylium ion pair that undergoes subsequent cycloaddition with high enantioselectivity.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3173575PMC
http://dx.doi.org/10.1021/ja206997eDOI Listing

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