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Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes
A novel nickel-catalyzed asymmetric 1,2-vinylboration reaction has been developed to afford benzylic alkenylboration products with high yields and excellent enantioselectivities by using a chiral bisoxazoline ligand. Under optimized conditions, a wide variety of chiral 2-boryl-1,1-arylvinylalkanes a...
Autores principales: | , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8513998/ https://www.ncbi.nlm.nih.gov/pubmed/34745552 http://dx.doi.org/10.1039/d1sc04071e |
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author | Ye, Yang Liu, Jiandong Xu, Bing Jiang, Songwei Bai, Renren Li, Shijun Xie, Tian Ye, Xiang-Yang |
author_facet | Ye, Yang Liu, Jiandong Xu, Bing Jiang, Songwei Bai, Renren Li, Shijun Xie, Tian Ye, Xiang-Yang |
author_sort | Ye, Yang |
collection | PubMed |
description | A novel nickel-catalyzed asymmetric 1,2-vinylboration reaction has been developed to afford benzylic alkenylboration products with high yields and excellent enantioselectivities by using a chiral bisoxazoline ligand. Under optimized conditions, a wide variety of chiral 2-boryl-1,1-arylvinylalkanes are efficiently prepared from readily available olefins and vinyl halides in the presence of bis(pinacolato)diboron as the boron source in a mild and easy-to-operate manner. This three-component cascade protocol furnishes exceptional chemo- and stereoselectivity, and its usefulness is illustrated by its application in asymmetric modifications of several structurally complex natural products and pharmaceuticals. |
format | Online Article Text |
id | pubmed-8513998 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-85139982021-11-04 Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes Ye, Yang Liu, Jiandong Xu, Bing Jiang, Songwei Bai, Renren Li, Shijun Xie, Tian Ye, Xiang-Yang Chem Sci Chemistry A novel nickel-catalyzed asymmetric 1,2-vinylboration reaction has been developed to afford benzylic alkenylboration products with high yields and excellent enantioselectivities by using a chiral bisoxazoline ligand. Under optimized conditions, a wide variety of chiral 2-boryl-1,1-arylvinylalkanes are efficiently prepared from readily available olefins and vinyl halides in the presence of bis(pinacolato)diboron as the boron source in a mild and easy-to-operate manner. This three-component cascade protocol furnishes exceptional chemo- and stereoselectivity, and its usefulness is illustrated by its application in asymmetric modifications of several structurally complex natural products and pharmaceuticals. The Royal Society of Chemistry 2021-09-07 /pmc/articles/PMC8513998/ /pubmed/34745552 http://dx.doi.org/10.1039/d1sc04071e Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Ye, Yang Liu, Jiandong Xu, Bing Jiang, Songwei Bai, Renren Li, Shijun Xie, Tian Ye, Xiang-Yang Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes |
title | Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes |
title_full | Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes |
title_fullStr | Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes |
title_full_unstemmed | Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes |
title_short | Nickel-catalyzed enantioselective 1,2-vinylboration of styrenes |
title_sort | nickel-catalyzed enantioselective 1,2-vinylboration of styrenes |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8513998/ https://www.ncbi.nlm.nih.gov/pubmed/34745552 http://dx.doi.org/10.1039/d1sc04071e |
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