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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...

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Autores principales: Sikandar, Sana, Zahoor, Ameer Fawad, Ghaffar, Abdul, Anjum, Muhammad Naveed, Noreen, Razia, Irfan, Ali, Munir, Bushra, Kotwica-Mojzych, Katarzyna, Mojzych, Mariusz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
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.
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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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