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Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products
Enantioenriched α-aminoboronic acids play a unique role in medicinal chemistry and have emerged as privileged pharmacophores in proteasome inhibitors. Additionally, they represent synthetically useful chiral building blocks in organic synthesis. Recently, CuH-catalyzed asymmetric alkene hydrofunctio...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7227802/ https://www.ncbi.nlm.nih.gov/pubmed/32420528 http://dx.doi.org/10.1038/s41929-019-0384-6 |
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author | Gao, De-Wei Gao, Yang Shao, Huiling Qiao, Tian-Zhang Wang, Xin Sanchez, Brittany B. Chen, Jason S. Liu, Peng Engle, Keary M. |
author_facet | Gao, De-Wei Gao, Yang Shao, Huiling Qiao, Tian-Zhang Wang, Xin Sanchez, Brittany B. Chen, Jason S. Liu, Peng Engle, Keary M. |
author_sort | Gao, De-Wei |
collection | PubMed |
description | Enantioenriched α-aminoboronic acids play a unique role in medicinal chemistry and have emerged as privileged pharmacophores in proteasome inhibitors. Additionally, they represent synthetically useful chiral building blocks in organic synthesis. Recently, CuH-catalyzed asymmetric alkene hydrofunctionalization has become a powerful tool to construct stereogenic carbon centers. In contrast, applying CuH cascade catalysis to achieve reductive 1,1-difunctionalization of alkynes remains an important, but largely unaddressed, synthetic challenge. Herein, we report an efficient strategy to synthesize α-aminoboronates via CuH-catalyzed hydroboration/hydroamination cascade of readily available alkynes. Notably, this transformation selectively delivers the desired 1,1-heterodifunctionalized product in favor of alternative homodifunctionalized, 1,2-heterodifunctionalized, or reductively monofunctionalized byproducts, thereby offering rapid access to these privileged scaffolds with high chemo-, regio- and enantioselectivity. |
format | Online Article Text |
id | pubmed-7227802 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
record_format | MEDLINE/PubMed |
spelling | pubmed-72278022020-07-01 Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products Gao, De-Wei Gao, Yang Shao, Huiling Qiao, Tian-Zhang Wang, Xin Sanchez, Brittany B. Chen, Jason S. Liu, Peng Engle, Keary M. Nat Catal Article Enantioenriched α-aminoboronic acids play a unique role in medicinal chemistry and have emerged as privileged pharmacophores in proteasome inhibitors. Additionally, they represent synthetically useful chiral building blocks in organic synthesis. Recently, CuH-catalyzed asymmetric alkene hydrofunctionalization has become a powerful tool to construct stereogenic carbon centers. In contrast, applying CuH cascade catalysis to achieve reductive 1,1-difunctionalization of alkynes remains an important, but largely unaddressed, synthetic challenge. Herein, we report an efficient strategy to synthesize α-aminoboronates via CuH-catalyzed hydroboration/hydroamination cascade of readily available alkynes. Notably, this transformation selectively delivers the desired 1,1-heterodifunctionalized product in favor of alternative homodifunctionalized, 1,2-heterodifunctionalized, or reductively monofunctionalized byproducts, thereby offering rapid access to these privileged scaffolds with high chemo-, regio- and enantioselectivity. 2019-12-02 2020 /pmc/articles/PMC7227802/ /pubmed/32420528 http://dx.doi.org/10.1038/s41929-019-0384-6 Text en Users may view, print, copy, and download text and data-mine the content in such documents, for the purposes of academic research, subject always to the full Conditions of use:http://www.nature.com/authors/editorial_policies/license.html#terms |
spellingShingle | Article Gao, De-Wei Gao, Yang Shao, Huiling Qiao, Tian-Zhang Wang, Xin Sanchez, Brittany B. Chen, Jason S. Liu, Peng Engle, Keary M. Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products |
title | Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products |
title_full | Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products |
title_fullStr | Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products |
title_full_unstemmed | Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products |
title_short | Cascade CuH-Catalysed Conversion of Alkynes to Enantioenriched 1,1-Disubstituted Products |
title_sort | cascade cuh-catalysed conversion of alkynes to enantioenriched 1,1-disubstituted products |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7227802/ https://www.ncbi.nlm.nih.gov/pubmed/32420528 http://dx.doi.org/10.1038/s41929-019-0384-6 |
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