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Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives
Chiral β‐aminoalkylzinc halides were prepared starting from optically pure commercial β‐amino‐alcohols. These amino‐alcohols were converted to the corresponding N‐pyrrolyl‐protected alkyl iodides which undergo a zinc insertion in the presence of LiCl (THF, 25 °C, 10–90 min). Subsequent Negishi cross...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497206/ https://www.ncbi.nlm.nih.gov/pubmed/32196786 http://dx.doi.org/10.1002/chem.202000870 |
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author | Leroux, Marcel Huang, Wan‐Yun Lemke, Yannick Koller, Thaddäus J. Karaghiosoff, Konstantin Knochel, Paul |
author_facet | Leroux, Marcel Huang, Wan‐Yun Lemke, Yannick Koller, Thaddäus J. Karaghiosoff, Konstantin Knochel, Paul |
author_sort | Leroux, Marcel |
collection | PubMed |
description | Chiral β‐aminoalkylzinc halides were prepared starting from optically pure commercial β‐amino‐alcohols. These amino‐alcohols were converted to the corresponding N‐pyrrolyl‐protected alkyl iodides which undergo a zinc insertion in the presence of LiCl (THF, 25 °C, 10–90 min). Subsequent Negishi cross‐coupling or acylation reactions with acid chlorides produced amino‐derivatives with retention of chirality. Diastereoselective CBS‐reductions of some prepared N‐pyrrolyl‐ketones provided 1,3‐subsituted N‐pyrrolyl‐alcohols with high diastereoselectivity. Additionally, a deprotection procedure involving an ozonolysis allowed the conversion of the pyrrole‐ring into a formamide without loss of optical purity. |
format | Online Article Text |
id | pubmed-7497206 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-74972062020-09-25 Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives Leroux, Marcel Huang, Wan‐Yun Lemke, Yannick Koller, Thaddäus J. Karaghiosoff, Konstantin Knochel, Paul Chemistry Full Papers Chiral β‐aminoalkylzinc halides were prepared starting from optically pure commercial β‐amino‐alcohols. These amino‐alcohols were converted to the corresponding N‐pyrrolyl‐protected alkyl iodides which undergo a zinc insertion in the presence of LiCl (THF, 25 °C, 10–90 min). Subsequent Negishi cross‐coupling or acylation reactions with acid chlorides produced amino‐derivatives with retention of chirality. Diastereoselective CBS‐reductions of some prepared N‐pyrrolyl‐ketones provided 1,3‐subsituted N‐pyrrolyl‐alcohols with high diastereoselectivity. Additionally, a deprotection procedure involving an ozonolysis allowed the conversion of the pyrrole‐ring into a formamide without loss of optical purity. John Wiley and Sons Inc. 2020-06-29 2020-07-22 /pmc/articles/PMC7497206/ /pubmed/32196786 http://dx.doi.org/10.1002/chem.202000870 Text en © 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made. |
spellingShingle | Full Papers Leroux, Marcel Huang, Wan‐Yun Lemke, Yannick Koller, Thaddäus J. Karaghiosoff, Konstantin Knochel, Paul Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives |
title | Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives |
title_full | Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives |
title_fullStr | Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives |
title_full_unstemmed | Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives |
title_short | Pyrrole‐Protected β‐Aminoalkylzinc Reagents for the Enantioselective Synthesis of Amino‐Derivatives |
title_sort | pyrrole‐protected β‐aminoalkylzinc reagents for the enantioselective synthesis of amino‐derivatives |
topic | Full Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7497206/ https://www.ncbi.nlm.nih.gov/pubmed/32196786 http://dx.doi.org/10.1002/chem.202000870 |
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