Exploiting the imidazolium effect in base-free ammonium enolate generation : synthetic and mechanistic studies
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N-Acyl imidazoles and catalytic isothiourea hydrochloride salts function as ammonium enolate precursors in the absence of base. Enantioselective Michael addition-cyclization reactions using different α,β-unsaturated Michael acceptors have been performed to form dihydropyranones and dihydropyridinones with high stereoselectivity. Detailed mechanistic studies using RPKA have revealed the importance of the “imidazolium” effect in ammonium enolate formation and have highlighted key differences with traditional base-mediated processes.
Young , C M , Stark , D G , West , T H , Taylor , J E & Smith , A D 2016 , ' Exploiting the imidazolium effect in base-free ammonium enolate generation : synthetic and mechanistic studies ' Angewandte Chemie International Edition , vol 55 , no. 46 , pp. 14394-14399 . DOI: 10.1002/anie.201608046
Angewandte Chemie International Edition
Copyright © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://doi.org/10.1002/anie.201608046
The authors thank the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement no. 279850 (CMY, THW, JET). ADS thanks the Royal Society for a Wolfson Merit Award.
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