Kinetic Resolution and Dynamic Kinetic Resolution of Chromene by Rhodium‐Catalyzed Asymmetric Hydroarylation

A highly efficient kinetic resolution and dynamic kinetic resolution of chromene is reported for the first time and they procced by a rhodium‐catalyzed asymmetric hydroarylation pathway. This new approach offers versatile access to various chiral 2,3‐diaryl‐chromanes containing vicinal stereogenic c...

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Veröffentlicht in:Angewandte Chemie International Edition 2019-04, Vol.58 (16), p.5343-5347
Hauptverfasser: Yang, Qingjing, Wang, Yanbo, Luo, Shihui, Wang, Jun (Joelle)
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Sprache:eng
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Zusammenfassung:A highly efficient kinetic resolution and dynamic kinetic resolution of chromene is reported for the first time and they procced by a rhodium‐catalyzed asymmetric hydroarylation pathway. This new approach offers versatile access to various chiral 2,3‐diaryl‐chromanes containing vicinal stereogenic centers, as well as the recovered chiral flavenes, in high yields with excellent ee values (s factor up to 532). Particularly noteworthy is that this strategy can be further extended to the establishment of a dynamic version of the kinetic resolution of chromene acetals and allows complete access to chiral isoflavanes and α‐aryl hydrocoumarins. Dynamic! A highly efficient kinetic resolution of flavenes proceeds through a Rh‐catalyzed asymmetric hydroarylation pathway and offers versatile access to chiral 2,3‐diaryl‐chromenes containing vicinal stereogenic centers, as well as the recovered chiral flavenes, in high yields with excellent ee values (s factor up to 532). This strategy can be extended to the dynamic version of a kinetic resolution of chromene acetals.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201900721