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Issue 35, 2018
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Redox deracemization of 1,3,4,9-tetrahydropyrano[3,4-b]indoles

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Abstract

The existing asymmetric synthesis of enantiopure α-substituted cyclic ethers predominantly relies on the enantioselective C–C bond formation involving a prochiral oxocarbenium ion intermediate. In such a strategy, enantioselectivity and efficiency are typically susceptible to the electronic and substituent effects of either nucleophile or electrophile partners. Here, we describe a strategically different redox deracemization of α-substituted 1,3,4,9-tetrahydropyrano[3,4-b]indoles. This method exhibits good compatibility with the regional variation of the electronic or substituent effect of substrates, thus providing a practical and efficient supplement to the traditional strategy.

Graphical abstract: Redox deracemization of 1,3,4,9-tetrahydropyrano[3,4-b]indoles

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Publication details

The article was received on 13 Feb 2018, accepted on 05 Apr 2018 and first published on 05 Apr 2018


Article type: Communication
DOI: 10.1039/C8CC01276H
Citation: Chem. Commun., 2018,54, 4445-4448
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    Redox deracemization of 1,3,4,9-tetrahydropyrano[3,4-b]indoles

    R. Lu, Y. Li, J. Zhao, J. Li, S. Wang and L. Liu, Chem. Commun., 2018, 54, 4445
    DOI: 10.1039/C8CC01276H

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