Enantioselective Rhodium-Catalyzed Cycloisomerization of 1,6-Allenynes to access 5/6-Fused Bicycle[4.3.0]nonadienes
Transition-metal-catalyzed cycloisomerization of 1,n-allenynes represents a powerful synthetic tool to rapidly assemble complex polycyclic skeletons from simple linear substrates. Nevertheless, there are no reports of the asymmetric version of these reactions. Moreover, most of these reactions proce...
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| Published in | Nature communications Vol. 10; no. 1; pp. 949 - 10 |
|---|---|
| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
London
Nature Publishing Group UK
27.02.2019
Nature Publishing Group Nature Portfolio |
| Subjects | |
| Online Access | Get full text |
| ISSN | 2041-1723 2041-1723 |
| DOI | 10.1038/s41467-019-08900-z |
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| Abstract | Transition-metal-catalyzed cycloisomerization of 1,n-allenynes represents a powerful synthetic tool to rapidly assemble complex polycyclic skeletons from simple linear substrates. Nevertheless, there are no reports of the asymmetric version of these reactions. Moreover, most of these reactions proceed through a
6-endo-dig
cyclization pathway, which preferentially delivers the distal product (via 5/5 rhodacyclic intermediate) rather than the proximal one (via 6/5 rhodacyclic intermediate). Herein, we report an enantioselective rhodium(I)-catalyzed cycloisomerization of 1,6-allenynes to provide the proximal product 5/6-fused bicycle[4.3.0]nonadienes in good yields and with excellent enantioselectivities. Remarkably, this chemistry works perfectly for 1,6-allenynes having a cyclic substituent within the allene component, thereby affording synthetically formidable tricyclic products with excellent enantioselectivities. Moreover, extensive DFT calculations suggest an uncommon pathway involving 5-
exo
-
dig
cycloisomerization, ring-expansion, rate-determining alkene isomerization involving C
sp3
-H activation, C-C activation of the cyclobutene moiety and finally reductive elimination. Deuterium labeling experiments support the rate-determining step involving the C–H bond activation in this transformation.
Cycloisomerization of 1,n-allenynes allows to efficiently assembly polycyclic skeletons, however its asymmetric variant remains elusive. Here, the authors report the enantioselective Rh(I)-catalyzed cycloisomerization of 1,6-allenynes and disclose an uncommon 5-exo-dig pathway via DFT calculations. |
|---|---|
| AbstractList | Transition-metal-catalyzed cycloisomerization of 1,n-allenynes represents a powerful synthetic tool to rapidly assemble complex polycyclic skeletons from simple linear substrates. Nevertheless, there are no reports of the asymmetric version of these reactions. Moreover, most of these reactions proceed through a
6-endo-dig
cyclization pathway, which preferentially delivers the distal product (via 5/5 rhodacyclic intermediate) rather than the proximal one (via 6/5 rhodacyclic intermediate). Herein, we report an enantioselective rhodium(I)-catalyzed cycloisomerization of 1,6-allenynes to provide the proximal product 5/6-fused bicycle[4.3.0]nonadienes in good yields and with excellent enantioselectivities. Remarkably, this chemistry works perfectly for 1,6-allenynes having a cyclic substituent within the allene component, thereby affording synthetically formidable tricyclic products with excellent enantioselectivities. Moreover, extensive DFT calculations suggest an uncommon pathway involving 5-
exo
-
dig
cycloisomerization, ring-expansion, rate-determining alkene isomerization involving C
sp3
-H activation, C-C activation of the cyclobutene moiety and finally reductive elimination. Deuterium labeling experiments support the rate-determining step involving the C–H bond activation in this transformation.
Cycloisomerization of 1,n-allenynes allows to efficiently assembly polycyclic skeletons, however its asymmetric variant remains elusive. Here, the authors report the enantioselective Rh(I)-catalyzed cycloisomerization of 1,6-allenynes and disclose an uncommon 5-exo-dig pathway via DFT calculations. Transition-metal-catalyzed cycloisomerization of 1,n-allenynes represents a powerful synthetic tool to rapidly assemble complex polycyclic skeletons from simple linear substrates. Nevertheless, there are no reports of the asymmetric version of these reactions. Moreover, most of these reactions proceed through a 6-endo-dig cyclization pathway, which preferentially delivers the distal product (via 5/5 rhodacyclic intermediate) rather than the proximal one (via 6/5 rhodacyclic intermediate). Herein, we report an enantioselective rhodium(I)-catalyzed cycloisomerization of 1,6-allenynes to provide the proximal product 5/6-fused bicycle[4.3.0]nonadienes in good yields and with excellent enantioselectivities. Remarkably, this chemistry works perfectly for 1,6-allenynes having a cyclic substituent within the allene component, thereby affording synthetically formidable tricyclic products with excellent enantioselectivities. Moreover, extensive DFT calculations suggest an uncommon pathway involving 5-exo-dig cycloisomerization, ring-expansion, rate-determining alkene isomerization involving C -H activation, C-C activation of the cyclobutene moiety and finally reductive elimination. Deuterium labeling experiments support the rate-determining step involving the C-H bond activation in this transformation. Transition-metal-catalyzed cycloisomerization of 1,n-allenynes represents a powerful synthetic tool to rapidly assemble complex polycyclic skeletons from simple linear substrates. Nevertheless, there are no reports of the asymmetric version of these reactions. Moreover, most of these reactions proceed through a 6-endo-dig cyclization pathway, which preferentially delivers the distal product (via 5/5 rhodacyclic intermediate) rather than the proximal one (via 6/5 rhodacyclic intermediate). Herein, we report an enantioselective rhodium(I)-catalyzed cycloisomerization of 1,6-allenynes to provide the proximal product 5/6-fused bicycle[4.3.0]nonadienes in good yields and with excellent enantioselectivities. Remarkably, this chemistry works perfectly for 1,6-allenynes having a cyclic substituent within the allene component, thereby affording synthetically formidable tricyclic products with excellent enantioselectivities. Moreover, extensive DFT calculations suggest an uncommon pathway involving 5- exo - dig cycloisomerization, ring-expansion, rate-determining alkene isomerization involving C sp3 -H activation, C-C activation of the cyclobutene moiety and finally reductive elimination. Deuterium labeling experiments support the rate-determining step involving the C–H bond activation in this transformation. Transition-metal-catalyzed cycloisomerization of 1,n-allenynes represents a powerful synthetic tool to rapidly assemble complex polycyclic skeletons from simple linear substrates. Nevertheless, there are no reports of the asymmetric version of these reactions. Moreover, most of these reactions proceed through a 6-endo-dig cyclization pathway, which preferentially delivers the distal product (via 5/5 rhodacyclic intermediate) rather than the proximal one (via 6/5 rhodacyclic intermediate). Herein, we report an enantioselective rhodium(I)-catalyzed cycloisomerization of 1,6-allenynes to provide the proximal product 5/6-fused bicycle[4.3.0]nonadienes in good yields and with excellent enantioselectivities. Remarkably, this chemistry works perfectly for 1,6-allenynes having a cyclic substituent within the allene component, thereby affording synthetically formidable tricyclic products with excellent enantioselectivities. Moreover, extensive DFT calculations suggest an uncommon pathway involving 5-exo-dig cycloisomerization, ring-expansion, rate-determining alkene isomerization involving Csp3-H activation, C-C activation of the cyclobutene moiety and finally reductive elimination. Deuterium labeling experiments support the rate-determining step involving the C–H bond activation in this transformation.Cycloisomerization of 1,n-allenynes allows to efficiently assembly polycyclic skeletons, however its asymmetric variant remains elusive. Here, the authors report the enantioselective Rh(I)-catalyzed cycloisomerization of 1,6-allenynes and disclose an uncommon 5-exo-dig pathway via DFT calculations. Cycloisomerization of 1,n-allenynes allows to efficiently assembly polycyclic skeletons, however its asymmetric variant remains elusive. Here, the authors report the enantioselective Rh(I)-catalyzed cycloisomerization of 1,6-allenynes and disclose an uncommon 5-exo-dig pathway via DFT calculations. |
| ArticleNumber | 949 |
| Author | Deng, Xu Lan, Jialing Chung, Lung Wa Zhang, Xiaoyong Shi, Li-Yang Zhang, Xumu Guan, Yu-Qing Lv, Hui |
| Author_xml | – sequence: 1 givenname: Xu orcidid: 0000-0001-7683-1626 surname: Deng fullname: Deng, Xu organization: Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, College of Xiangya Pharmaceutical Sciences, Central South University, Key Laboratory of Biomedical Polymers of Ministry of Education & College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University – sequence: 2 givenname: Li-Yang surname: Shi fullname: Shi, Li-Yang organization: Key Laboratory of Biomedical Polymers of Ministry of Education & College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University – sequence: 3 givenname: Jialing surname: Lan fullname: Lan, Jialing organization: Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology, School of Chemistry and Chemical Engineering, Harbin Institute of Technology – sequence: 4 givenname: Yu-Qing surname: Guan fullname: Guan, Yu-Qing organization: Key Laboratory of Biomedical Polymers of Ministry of Education & College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University – sequence: 5 givenname: Xiaoyong orcidid: 0000-0002-0966-4343 surname: Zhang fullname: Zhang, Xiaoyong organization: Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology – sequence: 6 givenname: Hui orcidid: 0000-0003-1378-1945 surname: Lv fullname: Lv, Hui email: huilv@whu.edu.cn organization: Key Laboratory of Biomedical Polymers of Ministry of Education & College of Chemistry and Molecular Sciences, Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, Wuhan University – sequence: 7 givenname: Lung Wa orcidid: 0000-0001-9460-7812 surname: Chung fullname: Chung, Lung Wa email: oscarchung@sustc.edu.cn organization: Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology – sequence: 8 givenname: Xumu surname: Zhang fullname: Zhang, Xumu email: zhangxm@sustc.edu.cn organization: Shenzhen Grubbs Institute and Department of Chemistry, Southern University of Science and Technology |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/30814517$$D View this record in MEDLINE/PubMed |
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| Snippet | Transition-metal-catalyzed cycloisomerization of 1,n-allenynes represents a powerful synthetic tool to rapidly assemble complex polycyclic skeletons from... Cycloisomerization of 1,n-allenynes allows to efficiently assembly polycyclic skeletons, however its asymmetric variant remains elusive. Here, the authors... |
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| SubjectTerms | 140/131 140/58 639/638/403/934 639/638/549/933 639/638/77/883 Activation Allene Bicycles Catalysis Chemistry Deuterium Enantiomers Genetic transformation Humanities and Social Sciences Hydrogen bonds Isomerization Ligands multidisciplinary Organic chemistry Rhodium Science Science (multidisciplinary) Solvents Substrates Transition metals |
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| Title | Enantioselective Rhodium-Catalyzed Cycloisomerization of 1,6-Allenynes to access 5/6-Fused Bicycle[4.3.0]nonadienes |
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