Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions

Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions

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 c...

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Bibliographic Details
Published in:Journal of the American Chemical Society Vol. 133; no. 37; pp. 14578 - 14581
Main Authors: Burns, Noah Z, Witten, Michael R, Jacobsen, Eric N
Format: Journal Article
Language:English
Published: United States American Chemical Society 21-09-2011
Subjects:
Catalysis
Cyclization
Heterocyclic Compounds, Bridged-Ring - chemistry
Stereoisomerism
Thiourea - chemistry
Online Access:Get full text
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Summary: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.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja206997e