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Issue 26, 2018
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Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles

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Abstract

A copper(I)-catalyzed dearomative borylation of N-alkoxycarbonyl protected indole-3-carboxylates has been developed. The boron addition in this reaction occurred regioselectively at the 2-position of indoles followed by diastereoselective protonation, affording the corresponding stable cyclic chiral α-amino boronates (2-borylindolines) in moderate to good yields with excellent diastereo- and enantioselectivities. The product 2c could be used as a versatile precursor to undergo subsequent stereoselective transformations, delivering highly functionalized 2,3,3-trisubstituted chiral indolines.

Graphical abstract: Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles

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Publication details

The article was received on 20 Apr 2018, accepted on 08 Jun 2018 and first published on 12 Jun 2018


Article type: Edge Article
DOI: 10.1039/C8SC01815D
Citation: Chem. Sci., 2018,9, 5855-5859
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    Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles

    L. Chen, J. Shen, Q. Gao and S. Xu, Chem. Sci., 2018, 9, 5855
    DOI: 10.1039/C8SC01815D

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