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Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions
[Image: see text] Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti β-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric varian...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4033649/ https://www.ncbi.nlm.nih.gov/pubmed/24787904 http://dx.doi.org/10.1021/jo5003505 |
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author | Luan, Yi Yu, Jie Zhang, Xiaowei Schaus, Scott E. Wang, Ge |
author_facet | Luan, Yi Yu, Jie Zhang, Xiaowei Schaus, Scott E. Wang, Ge |
author_sort | Luan, Yi |
collection | PubMed |
description | [Image: see text] Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti β-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (−)-phenylmenthol as chiral auxiliary in good yield and selectivity. These β-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules. |
format | Online Article Text |
id | pubmed-4033649 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-40336492015-04-30 Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions Luan, Yi Yu, Jie Zhang, Xiaowei Schaus, Scott E. Wang, Ge J Org Chem [Image: see text] Diazo compounds, boranes, and acyl imines undergo a three-component Mannich condensation reaction under catalyst-free conditions to give the anti β-amino carbonyl compounds in high diastereoselectivity. The reaction tolerates a variety of functional groups, and an asymmetric variant was achieved using the (−)-phenylmenthol as chiral auxiliary in good yield and selectivity. These β-amino carbonyl compounds are valuable intermediates, which can be transformed to many potential bioactive molecules. American Chemical Society 2014-04-30 2014-05-16 /pmc/articles/PMC4033649/ /pubmed/24787904 http://dx.doi.org/10.1021/jo5003505 Text en Copyright © 2014 American Chemical Society |
spellingShingle | Luan, Yi Yu, Jie Zhang, Xiaowei Schaus, Scott E. Wang, Ge Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions |
title | Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions |
title_full | Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions |
title_fullStr | Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions |
title_full_unstemmed | Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions |
title_short | Diastereoselective Three-Component Synthesis of β-Amino Carbonyl Compounds Using Diazo Compounds, Boranes, and Acyl Imines under Catalyst-Free Conditions |
title_sort | diastereoselective three-component synthesis of β-amino carbonyl compounds using diazo compounds, boranes, and acyl imines under catalyst-free conditions |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4033649/ https://www.ncbi.nlm.nih.gov/pubmed/24787904 http://dx.doi.org/10.1021/jo5003505 |
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