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Royal Society of Chemistry, Chemical Communications, 17(53), p. 2555-2558

DOI: 10.1039/c6cc10178j

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6-exo-trig Michael addition-lactonizations for catalytic enantioselective chromenone synthesis

This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

The 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 ; 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. ; Publisher PDF ; Peer reviewed