Enantioselective Copper‐Catalyzed Formal [2+1] and [4+1] Annulations of Diynes with Ketones via Carbonyl Ylides
Carbonyl ylides have proven to be powerful synthons for the efficient construction of various valuable O‐heterocycles, and the formation of carbonyl ylides by the reaction of metal carbenes with carbonyls has attracted increasing attention over the past decades. However, a catalyst‐controlled highly...
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| Published in | Angewandte Chemie Vol. 134; no. 43 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
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24.10.2022
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| Abstract | Carbonyl ylides have proven to be powerful synthons for the efficient construction of various valuable O‐heterocycles, and the formation of carbonyl ylides by the reaction of metal carbenes with carbonyls has attracted increasing attention over the past decades. However, a catalyst‐controlled highly enantioselective reaction of carbonyl ylides from metal carbenes is extremely challenging. Herein, we report a novel copper‐catalyzed asymmetric formal [2+1] and [4+1] annulations of diynes with ketones via carbonyl ylides. Importantly, this protocol not only represents the first example of successful asymmetric epoxidation via carbonyl ylides, but also constitutes the first reaction of vinyl cations with carbonyl compounds. This method leads to the divergent, practical and atom‐economical synthesis of a range of chiral oxiranes and dihydrofurans in moderate to excellent yields with generally excellent enantioselectivities and diastereoselectivities via remote‐stereocontrol strategy.
A copper‐catalyzed asymmetric formal [2+1] and [4+1] annulations of diynes with ketones via carbonyl ylides is disclosed. This protocol enables the divergent, practical and atom‐economical synthesis of a range of chiral oxiranes and dihydrofurans in moderate to excellent yields with generally excellent enantioselectivities and diastereoselectivities. |
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| AbstractList | Carbonyl ylides have proven to be powerful synthons for the efficient construction of various valuable O‐heterocycles, and the formation of carbonyl ylides by the reaction of metal carbenes with carbonyls has attracted increasing attention over the past decades. However, a catalyst‐controlled highly enantioselective reaction of carbonyl ylides from metal carbenes is extremely challenging. Herein, we report a novel copper‐catalyzed asymmetric formal [2+1] and [4+1] annulations of diynes with ketones via carbonyl ylides. Importantly, this protocol not only represents the first example of successful asymmetric epoxidation via carbonyl ylides, but also constitutes the first reaction of vinyl cations with carbonyl compounds. This method leads to the divergent, practical and atom‐economical synthesis of a range of chiral oxiranes and dihydrofurans in moderate to excellent yields with generally excellent enantioselectivities and diastereoselectivities via remote‐stereocontrol strategy. Carbonyl ylides have proven to be powerful synthons for the efficient construction of various valuable O‐heterocycles, and the formation of carbonyl ylides by the reaction of metal carbenes with carbonyls has attracted increasing attention over the past decades. However, a catalyst‐controlled highly enantioselective reaction of carbonyl ylides from metal carbenes is extremely challenging. Herein, we report a novel copper‐catalyzed asymmetric formal [2+1] and [4+1] annulations of diynes with ketones via carbonyl ylides. Importantly, this protocol not only represents the first example of successful asymmetric epoxidation via carbonyl ylides, but also constitutes the first reaction of vinyl cations with carbonyl compounds. This method leads to the divergent, practical and atom‐economical synthesis of a range of chiral oxiranes and dihydrofurans in moderate to excellent yields with generally excellent enantioselectivities and diastereoselectivities via remote‐stereocontrol strategy. A copper‐catalyzed asymmetric formal [2+1] and [4+1] annulations of diynes with ketones via carbonyl ylides is disclosed. This protocol enables the divergent, practical and atom‐economical synthesis of a range of chiral oxiranes and dihydrofurans in moderate to excellent yields with generally excellent enantioselectivities and diastereoselectivities. |
| Author | Qi, Lin‐Jun Huang, Zheng‐Qi Jiang, Jia‐Tian Lu, Xin Li, Cui‐Ting Zhu, Xin‐Qi Ye, Long‐Wu |
| Author_xml | – sequence: 1 givenname: Lin‐Jun surname: Qi fullname: Qi, Lin‐Jun organization: Taizhou University – sequence: 2 givenname: Cui‐Ting surname: Li fullname: Li, Cui‐Ting organization: Xiamen University – sequence: 3 givenname: Zheng‐Qi surname: Huang fullname: Huang, Zheng‐Qi organization: Xiamen University – sequence: 4 givenname: Jia‐Tian surname: Jiang fullname: Jiang, Jia‐Tian organization: Xiamen University – sequence: 5 givenname: Xin‐Qi surname: Zhu fullname: Zhu, Xin‐Qi organization: Xiamen University – sequence: 6 givenname: Xin surname: Lu fullname: Lu, Xin email: xinlu@xmu.edu.cn organization: Xiamen University – sequence: 7 givenname: Long‐Wu orcidid: 0000-0003-3108-2611 surname: Ye fullname: Ye, Long‐Wu email: longwuye@xmu.edu.cn organization: Chinese Academy of Sciences |
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| Snippet | Carbonyl ylides have proven to be powerful synthons for the efficient construction of various valuable O‐heterocycles, and the formation of carbonyl ylides by... |
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| SubjectTerms | Alkynes Annulation Asymmetric Catalysis Asymmetry Carbenes Carbonyl compounds Carbonyl Ylides Carbonyls Catalysts Cations Chemistry Copper Divergence Enantiomers Epoxidation Heterocycles Ketones |
| Title | Enantioselective Copper‐Catalyzed Formal [2+1] and [4+1] Annulations of Diynes with Ketones via Carbonyl Ylides |
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