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Issue 15, 2019
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A versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes

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Abstract

We report the synthesis of enantiomerically enriched 1,4-benzodioxanes containing alkyl, aryl, heteroaryl, and/or carbonyl substituents at the 2-position. The starting 1,4-benzodioxines were readily synthesized via ring closing metathesis using an efficient nitro-Grela catalyst at ppm levels. Excellent enantioselectivities of up to 99:1 er were obtained by using the versatile catalyst system [Ir(cod)Cl]2/BIDIME-dimer in the asymmetric hydrogenation of 2-substituted 1,4-benzodioxines. Furthermore, DFT calculations reveal that the selectivity of the process is controlled by the protonation step; and coordinating groups on the substrate may alter the interaction with the catalyst, resulting in a change in the facial selectivity.

Graphical abstract: A versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes

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Publication details

The article was received on 16 Dec 2018, accepted on 12 Mar 2019 and first published on 13 Mar 2019


Article type: Edge Article
DOI: 10.1039/C8SC05612A
Citation: Chem. Sci., 2019,10, 4339-4345
  • Open access: Creative Commons BY-NC license
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    A versatile catalyst system for enantioselective synthesis of 2-substituted 1,4-benzodioxanes

    E. Chong, B. Qu, Y. Zhang, Z. P. Cannone, J. C. Leung, S. Tcyrulnikov, K. D. Nguyen, N. Haddad, S. Biswas, X. Hou, K. Kaczanowska, M. Chwalba, A. Tracz, S. Czarnocki, J. J. Song, M. C. Kozlowski and C. H. Senanayake, Chem. Sci., 2019, 10, 4339
    DOI: 10.1039/C8SC05612A

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