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

Lili Chen; Jun-Jian Shen; Qian Gao; Senmiao Xu

doi:10.1039/C8SC01815D

Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles†

Lili Chen,^a Jun-Jian Shen,^a Qian Gao^a and Senmiao Xu

*^ab

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* Corresponding authors

^a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Centre for Excellence in Molecular Synthesis, Suzhou Research Institute, Lanzhou Institute of Chemical Physics, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Lanzhou 730000, China
E-mail: senmiaoxu@licp.cas.cn

^b Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China

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.

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https://doi.org/10.1039/C8SC01815D

Submitted

20 Apr 2018

Accepted

08 Jun 2018

First published

12 Jun 2018

This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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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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Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles†

Abstract

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

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