6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis
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The catalytic enantioselective 6-exo-trig Michael addition-lactonization of enone-acid substrates to form cis-chromenones with high diastereo- and enantiocontrol was developed using the commercially available isothiourea tetramisole. An acidic workup proved necessary to minimize product epimerization and maximize product er, providing cis-chromenones in excellent yield, and with excellent diastereo- and enantioselectivity.
N P , R M , Cordes , D B , Slawin , A M Z & Smith , A D 2017 , ' 6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis ' , Chemical Communications , vol. 53 , no. 17 , pp. 2555-2558 . https://doi.org/10.1039/C6CC10178J
Copyright 2017 the Authors. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
DescriptionThe authors thank the EPSRC Centre for Doctoral Training in Critical Resource Catalysis (CRITICAT, grant code EP/L016419/1, RMNP) for funding.The European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC Grant Agreement No. 279850 is also acknowledged. ADS thanks the Royal Society for a Wolfson Research Merit Award
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