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Literature DB >> 26095335

Enantioselective Borylative Dearomatization of Indoles through Copper(I) Catalysis.

Koji Kubota¹, Keiichi Hayama¹, Hiroaki Iwamoto¹, Hajime Ito².

Abstract

The enantioselective borylative dearomatization of a heteroaromatic compound has been achieved using a copper(I) catalyst and a diboron reagent. This reaction involves the regio- and enantioselective addition of active borylcopper(I) species to indole-2-carboxylates, followed by the diastereoselective protonation of the resulting copper(I) enolate to give the corresponding chiral indolines, which bear consecutive stereogenic centers.

Entities: Chemical

Keywords: borylation; copper; dearomatization; enantioselective synthesis; indoles

Year: 2015 PMID： 26095335 DOI： 10.1002/anie.201502964

Source DB: PubMed Journal: Angew Chem Int Ed Engl ISSN： 1433-7851 Impact factor: 15.336

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Cited

7 in total

1. Umpolung Ala^B Reagents for the Synthesis of Non-Proteogenic Amino Acids, Peptides and Proteins.

Authors: Feng Zhu; Eric Miller; Wyatt C Powell; Kelly Johnson; Alexander Beggs; Garrett E Evenson; Maciej A Walczak
Journal: Angew Chem Int Ed Engl Date: 2022-06-23 Impact factor: 16.823

2. Organometallic Ala^M Reagents for Umpolung Peptide Diversification.

Authors: Feng Zhu; Wyatt C Powell; Ruiheng Jing; Maciej A Walczak
Journal: Chem Catal Date: 2021-06-28

3. Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation.

Authors: Duanyang Kong; Suna Han; Rui Wang; Meina Li; Guofu Zi; Guohua Hou
Journal: Chem Sci Date: 2017-04-19 Impact factor: 9.825

4. Metal-free borylative dearomatization of indoles: exploring the divergent reactivity of aminoborane C-H borylation catalysts.

Authors: Arumugam Jayaraman; Luis C Misal Castro; Vincent Desrosiers; Frédéric-Georges Fontaine
Journal: Chem Sci Date: 2018-05-07 Impact factor: 9.825

Enantioselective Borylative Dearomatization of Indoles through Copper(I) Catalysis.

1. Umpolung Ala^B Reagents for the Synthesis of Non-Proteogenic Amino Acids, Peptides and Proteins.

2. Organometallic Ala^M Reagents for Umpolung Peptide Diversification.

3. Kinetic resolution of racemic 2-substituted 1,2-dihydroquinolines via asymmetric Cu-catalyzed borylation.

4. Metal-free borylative dearomatization of indoles: exploring the divergent reactivity of aminoborane C-H borylation catalysts.

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

6. Copper-catalyzed enantioselective 1,2-borylation of 1,3-dienes.

7. Enantio- and diastereoselective conjugate borylation/Mannich cyclization.