Cycloaddition reactions of enoldiazo compounds
Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+ n ]-cycloadditions ( n = 3, 4) by the enol silyl ether units of enoldiazo compoun...
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| Published in | Chemical Society reviews Vol. 46; no. 17; pp. 5425 - 5443 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
England
29.08.2017
|
| Subjects | |
| Online Access | Get full text |
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| Abstract | Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+
n
]-cycloadditions (
n
= 3, 4) by the enol silyl ether units of enoldiazo compounds with retention of the diazo functionality to furnish α-cyclic-α-diazo compounds that are themselves subject to further transformations of the diazo functional group; (2) [3+
n
]-cycloadditions (
n
= 1-5) by metallo-enolcarbenes formed by catalytic dinitrogen extrusion from enoldiazo compounds; (3) [2+
n
]-cycloadditions (
n
= 3, 4) by donor-acceptor cyclopropenes generated
in situ
from enoldiazo compounds that produce cyclopropane-fused ring systems. The role of dirhodium(
ii
) and the emergence of copper(
i
) catalysts are described, as are the different outcomes of reactions initiated with these catalysts. This comprehensive review on cycloaddition reactions of enoldiazo compounds, with emphasis on methodology development, mechanistic insight, and catalyst-controlled chemodivergence, aims to provide inspiration for future discoveries in the field and to catalyze the application of enoldiazo reagents by the wider synthetic community.
A comprehensive review on cycloaddition reactions of enoldiazo compounds is presented with emphasis on methodology development and mechanistic insight. |
|---|---|
| AbstractList | Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+
n
]-cycloadditions (
n
= 3, 4) by the enol silyl ether units of enoldiazo compounds with retention of the diazo functionality to furnish α-cyclic-α-diazo compounds that are themselves subject to further transformations of the diazo functional group; (2) [3+
n
]-cycloadditions (
n
= 1–5) by metallo-enolcarbenes formed by catalytic dinitrogen extrusion from enoldiazo compounds; (3) [2+
n
]-cycloadditions (
n
= 3, 4) by donor–acceptor cyclopropenes generated
in situ
from enoldiazo compounds that produce cyclopropane-fused ring systems. The role of dirhodium(
ii
) and the emergence of copper(
i
) catalysts are described, as are the different outcomes of reactions initiated with these catalysts. This comprehensive review on cycloaddition reactions of enoldiazo compounds, with emphasis on methodology development, mechanistic insight, and catalyst-controlled chemodivergence, aims to provide inspiration for future discoveries in the field and to catalyze the application of enoldiazo reagents by the wider synthetic community. Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+n]-cycloadditions (n = 3, 4) by the enol silyl ether units of enoldiazo compounds with retention of the diazo functionality to furnish α-cyclic-α-diazo compounds that are themselves subject to further transformations of the diazo functional group; (2) [3+n]-cycloadditions (n = 1-5) by metallo-enolcarbenes formed by catalytic dinitrogen extrusion from enoldiazo compounds; (3) [2+n]-cycloadditions (n = 3, 4) by donor-acceptor cyclopropenes generated in situ from enoldiazo compounds that produce cyclopropane-fused ring systems. The role of dirhodium(ii) and the emergence of copper(i) catalysts are described, as are the different outcomes of reactions initiated with these catalysts. This comprehensive review on cycloaddition reactions of enoldiazo compounds, with emphasis on methodology development, mechanistic insight, and catalyst-controlled chemodivergence, aims to provide inspiration for future discoveries in the field and to catalyze the application of enoldiazo reagents by the wider synthetic community.Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+n]-cycloadditions (n = 3, 4) by the enol silyl ether units of enoldiazo compounds with retention of the diazo functionality to furnish α-cyclic-α-diazo compounds that are themselves subject to further transformations of the diazo functional group; (2) [3+n]-cycloadditions (n = 1-5) by metallo-enolcarbenes formed by catalytic dinitrogen extrusion from enoldiazo compounds; (3) [2+n]-cycloadditions (n = 3, 4) by donor-acceptor cyclopropenes generated in situ from enoldiazo compounds that produce cyclopropane-fused ring systems. The role of dirhodium(ii) and the emergence of copper(i) catalysts are described, as are the different outcomes of reactions initiated with these catalysts. This comprehensive review on cycloaddition reactions of enoldiazo compounds, with emphasis on methodology development, mechanistic insight, and catalyst-controlled chemodivergence, aims to provide inspiration for future discoveries in the field and to catalyze the application of enoldiazo reagents by the wider synthetic community. Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+ n ]-cycloadditions ( n = 3, 4) by the enol silyl ether units of enoldiazo compounds with retention of the diazo functionality to furnish α-cyclic-α-diazo compounds that are themselves subject to further transformations of the diazo functional group; (2) [3+ n ]-cycloadditions ( n = 1–5) by metallo-enolcarbenes formed by catalytic dinitrogen extrusion from enoldiazo compounds; (3) [2+ n ]-cycloadditions ( n = 3, 4) by donor–acceptor cyclopropenes generated in situ from enoldiazo compounds that produce cyclopropane-fused ring systems. The role of dirhodium(II) and the emergence of copper(I) catalysts are described, as are the different outcomes of reactions initiated with these catalysts. This comprehensive review on cycloaddition reactions of enoldiazo compounds, with emphasis on methodology development, mechanistic insight, and catalyst-controlled chemodivergence, aims to provide inspiration for future discoveries in the field and to catalyze the application of enoldiazo reagents by the wider synthetic community. A comprehensive review on cycloaddition reactions of enoldiazo compounds is presented with emphasis on methodology development and mechanistic insight. Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+n]-cycloadditions (n = 3, 4) by the enol silyl ether units of enoldiazo compounds with retention of the diazo functionality to furnish α-cyclic-α-diazo compounds that are themselves subject to further transformations of the diazo functional group; (2) [3+n]-cycloadditions (n = 1-5) by metallo-enolcarbenes formed by catalytic dinitrogen extrusion from enoldiazo compounds; (3) [2+n]-cycloadditions (n = 3, 4) by donor-acceptor cyclopropenes generated in situ from enoldiazo compounds that produce cyclopropane-fused ring systems. The role of dirhodium(ii) and the emergence of copper(i) catalysts are described, as are the different outcomes of reactions initiated with these catalysts. This comprehensive review on cycloaddition reactions of enoldiazo compounds, with emphasis on methodology development, mechanistic insight, and catalyst-controlled chemodivergence, aims to provide inspiration for future discoveries in the field and to catalyze the application of enoldiazo reagents by the wider synthetic community. Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+ n ]-cycloadditions ( n = 3, 4) by the enol silyl ether units of enoldiazo compounds with retention of the diazo functionality to furnish α-cyclic-α-diazo compounds that are themselves subject to further transformations of the diazo functional group; (2) [3+ n ]-cycloadditions ( n = 1-5) by metallo-enolcarbenes formed by catalytic dinitrogen extrusion from enoldiazo compounds; (3) [2+ n ]-cycloadditions ( n = 3, 4) by donor-acceptor cyclopropenes generated in situ from enoldiazo compounds that produce cyclopropane-fused ring systems. The role of dirhodium( ii ) and the emergence of copper( i ) catalysts are described, as are the different outcomes of reactions initiated with these catalysts. This comprehensive review on cycloaddition reactions of enoldiazo compounds, with emphasis on methodology development, mechanistic insight, and catalyst-controlled chemodivergence, aims to provide inspiration for future discoveries in the field and to catalyze the application of enoldiazo reagents by the wider synthetic community. A comprehensive review on cycloaddition reactions of enoldiazo compounds is presented with emphasis on methodology development and mechanistic insight. |
| Author | Deng, Yongming Lankelma, Marianne Doyle, Michael P Cheng, Qing-Qing |
| AuthorAffiliation | Department of Chemistry The University of Texas at San Antonio |
| AuthorAffiliation_xml | – name: The University of Texas at San Antonio – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Qing-Qing surname: Cheng fullname: Cheng, Qing-Qing – sequence: 2 givenname: Yongming surname: Deng fullname: Deng, Yongming – sequence: 3 givenname: Marianne surname: Lankelma fullname: Lankelma, Marianne – sequence: 4 givenname: Michael P surname: Doyle fullname: Doyle, Michael P |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/28726896$$D View this record in MEDLINE/PubMed |
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| Notes | Michael P. (Mike) Doyle is the Rita and John Feik Distinguished University Chair in Medicinal Chemistry at the University of Texas at San Antonio. He is a graduate of the College of St. Thomas and Iowa State University, has had academic appointments at undergraduate institutions (Hope College and Trinity University) and graduate universities (University of Arizona and University of Maryland), as well as being Vice President, then President, of a science foundation (Research Corporation) before taking his current position. Doyle is a Fellow of the American Chemical Society, the American Association for the Advancement of Science, and the Royal Society of Chemistry, and he is widely recognized for his research in catalytic methods for metal carbene transformations. Qing-Qing Cheng was born in Binzhou of Shandong province, China in 1987. He received his BSc from Tianjin University in 2009. Then he began his graduate study at Nankai University under the supervision of Professor Qi-Lin Zhou, and obtained his PhD in organic chemistry in 2014. Subsequently, he joined the research group of Professor Michael P. Doyle at the University of Texas at San Antonio as a postdoctoral fellow. His research interests include the development of synthetic methodologies and their application in the syntheses of biologically active products, asymmetric catalysis, and medicinal chemistry. His current research in the Doyle group has focused on highly selective catalytic metal carbene transformations, in particular the cycloaddition reactions of enoldiazo compounds. Yongming Deng received his BSc from Shandong University in 2009. In 2014, he obtained his PhD from Miami University (Ohio) under the supervision of Dr Hong Wang. At MIAMI, he was engaged in the development of enamine/metal Lewis acid cooperative catalysis for new chemical reactions discovery. In the same year, he began his postdoctoral studies with Professor Michael P. Doyle at University of Maryland then moved to the University of Texas at San Antonio. His research in the Doyle group has focused on developing assessments of new catalysts and reagents to access catalytic metal carbene reactions and on investigating selective catalytic transformations of enoldiazo compounds. Marianne Lankelma (1994) obtained her BS and MS degrees from the University of Amsterdam, with a specialization in molecular design, synthesis, and catalysis. After her undergraduate project in the group of Prof. Dr Olivia Reinaud (Université Paris Descartes) and her graduate project in the group of Prof. Dr Joost N. H. Reek (University of Amsterdam), she completed her studies with an extracurricular internship in the group of Prof. Dr Michael P. Doyle at the University of Texas at San Antonio. Currently she investigates rhodium-mediated carbene (C1) polymerization as a PhD student under the supervision of Prof. Dr Bas de Bruin at the University of Amsterdam. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 ObjectType-Review-3 content type line 23 |
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| Snippet | Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles... |
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| SubjectTerms | amides catalysts copper cycloaddition reactions diazo compounds enols esters extrusion moieties nitrogen |
| Title | Cycloaddition reactions of enoldiazo compounds |
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