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Facile Access To Chiral 4-substituted Chromanes Through Rh-catalyzed Asymmetric Hydrogenation

Lin Tao, Q. Zhao, Q. Zhao, X. Zhang, X. Zhang, Xiu-Qin Dong
Published 2020 · Chemistry

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Abstract Rh/ZhaoPhos-catalyzed asymmetric hydrogenation of a series of (E)-2-(chroman-4-ylidene)acetates was successfully developed to prepare various chiral 4-substituted chromanes with high yields and excellent enantioselectivities (up to 99% yield, 98% ee). Moreover, the gram-scale hydrogenation could be performed well in the presence of 0.02 mol% catalyst loading (TON = 5000), the hydrogenation product was easily converted to access other important compounds, which demonstrated the synthetic utility of this asymmetric catalytic methodology.
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