Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans
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A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported. Commercially available (S)-(-)-tetramisole hydrochloride gives products with high syn diastereoselectivity in excellent enantioselectivity (up to 99:1 d.r. , 99% ee), whereas using a cinchona alkaloid derived catalyst gives the corresponding anti-diastereoisomers as the major product (up to 10:90 d.r., 99% ee). You can have it both ways! A stereodivergent asymmetric Lewis base catalyzed Michael addition/lactonization of enone acids into substituted dihydrobenzofuran and tetrahydrofuran derivatives is reported, giving products with high d.r. and ee (see scheme).
Belmessieri , D , De La Houpliere , A , Calder , E D D , Taylor , J E & Smith , A D 2014 , ' Stereodivergent organocatalytic intramolecular michael addition/ lactonization for the asymmetric synthesis of substituted dihydrobenzofurans and tetrahydrofurans ' Chemistry - A European Journal , vol 20 , no. 31 , pp. 9762-9769 . DOI: 10.1002/chem.201402684
Chemistry - A European Journal
© 2014 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
The authors thank the Royal Society for a University Research Fellowship (A.D.S.), the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007–2013), ERC Grant Agreement No. 279850 (A.D.L.H. and J.E.T.), and the EPSRC (DTA studentship to D.B.) for funding.
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