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Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles
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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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Royal Society of Chemistry
2018
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6050576/ https://www.ncbi.nlm.nih.gov/pubmed/30079199 http://dx.doi.org/10.1039/c8sc01815d |
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author | Chen, Lili Shen, Jun-Jian Gao, Qian Xu, Senmiao |
author_facet | Chen, Lili Shen, Jun-Jian Gao, Qian Xu, Senmiao |
author_sort | Chen, Lili |
collection | PubMed |
description | 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. |
format | Online Article Text |
id | pubmed-6050576 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-60505762018-08-03 Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles Chen, Lili Shen, Jun-Jian Gao, Qian Xu, Senmiao Chem Sci Chemistry 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. Royal Society of Chemistry 2018-06-12 /pmc/articles/PMC6050576/ /pubmed/30079199 http://dx.doi.org/10.1039/c8sc01815d Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0) |
spellingShingle | Chemistry Chen, Lili Shen, Jun-Jian Gao, Qian Xu, Senmiao Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles |
title | Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles
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title_full | Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles
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title_fullStr | Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles
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title_full_unstemmed | Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles
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title_short | Synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles
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title_sort | synthesis of cyclic chiral α-amino boronates by copper-catalyzed asymmetric dearomative borylation of indoles |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6050576/ https://www.ncbi.nlm.nih.gov/pubmed/30079199 http://dx.doi.org/10.1039/c8sc01815d |
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