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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...

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Autores principales: Luan, Yi, Yu, Jie, Zhang, Xiaowei, Schaus, Scott E., Wang, Ge
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
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.
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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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