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Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review
Allenes with two carbon–carbon double bonds belong to a unique class of unsaturated hydrocarbons. The central carbon atom of allene is sp hybridized and forms two σ-bonds and two π-bonds with two terminal sp(2) hybridized carbon atoms. The chemistry of allenes has been well documented over the last...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9860688/ https://www.ncbi.nlm.nih.gov/pubmed/36677762 http://dx.doi.org/10.3390/molecules28020704 |
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author | Sikandar, Sana Zahoor, Ameer Fawad Ghaffar, Abdul Anjum, Muhammad Naveed Noreen, Razia Irfan, Ali Munir, Bushra Kotwica-Mojzych, Katarzyna Mojzych, Mariusz |
author_facet | Sikandar, Sana Zahoor, Ameer Fawad Ghaffar, Abdul Anjum, Muhammad Naveed Noreen, Razia Irfan, Ali Munir, Bushra Kotwica-Mojzych, Katarzyna Mojzych, Mariusz |
author_sort | Sikandar, Sana |
collection | PubMed |
description | Allenes with two carbon–carbon double bonds belong to a unique class of unsaturated hydrocarbons. The central carbon atom of allene is sp hybridized and forms two σ-bonds and two π-bonds with two terminal sp(2) hybridized carbon atoms. The chemistry of allenes has been well documented over the last decades. They are more reactive than alkenes due to higher strain and exhibit significant axial chirality, thus playing a vital role in asymmetric synthesis. Over a variety of organic transformations, allenes specifically undergo classical metal catalyzed cycloaddition reactions to obtain chemo-, regio- and stereoselective cycloadducts. This review briefly describes different types of annulations including [2+2], [2+2+1], [3+2], [2+2+2], [4+2], [5+2], [6+2] cycloadditions using titanium, cobalt, rhodium, nickel, palladium, platinum, gold and phosphine catalyzed reactions along with a mechanistic study of some highlighted protocols. The synthetic applications of these reactions towards the synthesis of natural products such as aristeromycin, ent-[3]-ladderanol, waihoensene(−)-vindoline and (+)-4-epi-vindoline have also been described. |
format | Online Article Text |
id | pubmed-9860688 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-98606882023-01-22 Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review Sikandar, Sana Zahoor, Ameer Fawad Ghaffar, Abdul Anjum, Muhammad Naveed Noreen, Razia Irfan, Ali Munir, Bushra Kotwica-Mojzych, Katarzyna Mojzych, Mariusz Molecules Review Allenes with two carbon–carbon double bonds belong to a unique class of unsaturated hydrocarbons. The central carbon atom of allene is sp hybridized and forms two σ-bonds and two π-bonds with two terminal sp(2) hybridized carbon atoms. The chemistry of allenes has been well documented over the last decades. They are more reactive than alkenes due to higher strain and exhibit significant axial chirality, thus playing a vital role in asymmetric synthesis. Over a variety of organic transformations, allenes specifically undergo classical metal catalyzed cycloaddition reactions to obtain chemo-, regio- and stereoselective cycloadducts. This review briefly describes different types of annulations including [2+2], [2+2+1], [3+2], [2+2+2], [4+2], [5+2], [6+2] cycloadditions using titanium, cobalt, rhodium, nickel, palladium, platinum, gold and phosphine catalyzed reactions along with a mechanistic study of some highlighted protocols. The synthetic applications of these reactions towards the synthesis of natural products such as aristeromycin, ent-[3]-ladderanol, waihoensene(−)-vindoline and (+)-4-epi-vindoline have also been described. MDPI 2023-01-10 /pmc/articles/PMC9860688/ /pubmed/36677762 http://dx.doi.org/10.3390/molecules28020704 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Review Sikandar, Sana Zahoor, Ameer Fawad Ghaffar, Abdul Anjum, Muhammad Naveed Noreen, Razia Irfan, Ali Munir, Bushra Kotwica-Mojzych, Katarzyna Mojzych, Mariusz Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review |
title | Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review |
title_full | Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review |
title_fullStr | Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review |
title_full_unstemmed | Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review |
title_short | Unveiling the Chemistry and Synthetic Potential of Catalytic Cycloaddition Reaction of Allenes: A Review |
title_sort | unveiling the chemistry and synthetic potential of catalytic cycloaddition reaction of allenes: a review |
topic | Review |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9860688/ https://www.ncbi.nlm.nih.gov/pubmed/36677762 http://dx.doi.org/10.3390/molecules28020704 |
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