Issue 26, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2018,9, 5855-5859

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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