Copper‐Catalyzed Enantio‐ and Diastereoselective Addition of Silicon Nucleophiles to 3,3‐Disubstituted Cyclopropenes

A highly stereocontrolled syn‐addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper‐catalyzed C−Si...

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Detalles Bibliográficos
Autores principales: Zhang, Liangliang, Oestreich, Martin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6899982/
https://www.ncbi.nlm.nih.gov/pubmed/31531992
http://dx.doi.org/10.1002/chem.201904272
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author Zhang, Liangliang
Oestreich, Martin
author_facet Zhang, Liangliang
Oestreich, Martin
author_sort Zhang, Liangliang
collection PubMed
description A highly stereocontrolled syn‐addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper‐catalyzed C−Si bond formation closes the gap of the direct synthesis of α‐chiral cyclopropylsilanes.
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spelling pubmed-68999822019-12-20 Copper‐Catalyzed Enantio‐ and Diastereoselective Addition of Silicon Nucleophiles to 3,3‐Disubstituted Cyclopropenes Zhang, Liangliang Oestreich, Martin Chemistry Communications A highly stereocontrolled syn‐addition of silicon nucleophiles across cyclopropenes with two different geminal substituents at C3 is reported. Diastereomeric ratios are excellent throughout (d.r.≥98:2) and enantiomeric excesses usually higher than 90 %, even reaching 99 %. This copper‐catalyzed C−Si bond formation closes the gap of the direct synthesis of α‐chiral cyclopropylsilanes. John Wiley and Sons Inc. 2019-10-22 2019-11-13 /pmc/articles/PMC6899982/ /pubmed/31531992 http://dx.doi.org/10.1002/chem.201904272 Text en © 2019 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/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Zhang, Liangliang
Oestreich, Martin
Copper‐Catalyzed Enantio‐ and Diastereoselective Addition of Silicon Nucleophiles to 3,3‐Disubstituted Cyclopropenes
title Copper‐Catalyzed Enantio‐ and Diastereoselective Addition of Silicon Nucleophiles to 3,3‐Disubstituted Cyclopropenes
title_full Copper‐Catalyzed Enantio‐ and Diastereoselective Addition of Silicon Nucleophiles to 3,3‐Disubstituted Cyclopropenes
title_fullStr Copper‐Catalyzed Enantio‐ and Diastereoselective Addition of Silicon Nucleophiles to 3,3‐Disubstituted Cyclopropenes
title_full_unstemmed Copper‐Catalyzed Enantio‐ and Diastereoselective Addition of Silicon Nucleophiles to 3,3‐Disubstituted Cyclopropenes
title_short Copper‐Catalyzed Enantio‐ and Diastereoselective Addition of Silicon Nucleophiles to 3,3‐Disubstituted Cyclopropenes
title_sort copper‐catalyzed enantio‐ and diastereoselective addition of silicon nucleophiles to 3,3‐disubstituted cyclopropenes
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6899982/
https://www.ncbi.nlm.nih.gov/pubmed/31531992
http://dx.doi.org/10.1002/chem.201904272
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AT oestreichmartin coppercatalyzedenantioanddiastereoselectiveadditionofsiliconnucleophilesto33disubstitutedcyclopropenes

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