Stereodivergent Construction of 1,4‐Nonadjacent Stereocenters via Hydroalkylation of Racemic Allylic Alcohols Enabled by Copper/Ruthenium Relay Catalysis
An unprecedented hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by Cu/Ru relay catalysis has been developed via merging the ruthenium‐catalyzed asymmetric borrowing‐hydrogen reaction with a copper‐catalyzed asymmetric Michael addition in a one‐pot procedure. The curr...
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| Published in | Angewandte Chemie International Edition Vol. 61; no. 36; pp. e202206517 - n/a |
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| Main Authors | , , , , , |
| Format | Journal Article |
| Language | English |
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| Abstract | An unprecedented hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by Cu/Ru relay catalysis has been developed via merging the ruthenium‐catalyzed asymmetric borrowing‐hydrogen reaction with a copper‐catalyzed asymmetric Michael addition in a one‐pot procedure. The current method enables the efficient preparation of highly functionalized δ‐hydroxyesters bearing 1,4‐nonadjacent stereocenters in good yields with high levels of diastereoselectivity and excellent enantioselectivity under mild reaction conditions. The full complement of the four stereoisomers of hydroalkylation products could be readily accessed by orthogonal permutations of two chiral metal catalysts. The current work highlights the power of relay catalysis for the stereodivergent construction of 1,4‐nonadjacent stereocenters that were otherwise inaccessible.
An unprecedented stereodivergent hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by dual Cu/Ru relay catalysis has been developed. Merging the ruthenium‐catalyzed asymmetric borrowing‐hydrogen reaction with a copper‐catalyzed asymmetric Michael addition into a one‐pot procedure provided a route to highly functionalized δ‐hydroxyesters bearing 1,4‐nonadjacent stereocenters in good yields with excellent stereoselectivity under mild reaction conditions. |
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| AbstractList | An unprecedented hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by Cu/Ru relay catalysis has been developed via merging the ruthenium-catalyzed asymmetric borrowing-hydrogen reaction with a copper-catalyzed asymmetric Michael addition in a one-pot procedure. The current method enables the efficient preparation of highly functionalized delta-hydroxyesters bearing 1,4-nonadjacent stereocenters in good yields with high levels of diastereoselectivity and excellent enantioselectivity under mild reaction conditions. The full complement of the four stereoisomers of hydroalkylation products could be readily accessed by orthogonal permutations of two chiral metal catalysts. The current work highlights the power of relay catalysis for the stereodivergent construction of 1,4-nonadjacent stereocenters that were otherwise inaccessible. An unprecedented hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by Cu/Ru relay catalysis has been developed via merging the ruthenium‐catalyzed asymmetric borrowing‐hydrogen reaction with a copper‐catalyzed asymmetric Michael addition in a one‐pot procedure. The current method enables the efficient preparation of highly functionalized δ‐hydroxyesters bearing 1,4‐nonadjacent stereocenters in good yields with high levels of diastereoselectivity and excellent enantioselectivity under mild reaction conditions. The full complement of the four stereoisomers of hydroalkylation products could be readily accessed by orthogonal permutations of two chiral metal catalysts. The current work highlights the power of relay catalysis for the stereodivergent construction of 1,4‐nonadjacent stereocenters that were otherwise inaccessible. An unprecedented stereodivergent hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by dual Cu/Ru relay catalysis has been developed. Merging the ruthenium‐catalyzed asymmetric borrowing‐hydrogen reaction with a copper‐catalyzed asymmetric Michael addition into a one‐pot procedure provided a route to highly functionalized δ‐hydroxyesters bearing 1,4‐nonadjacent stereocenters in good yields with excellent stereoselectivity under mild reaction conditions. An unprecedented hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by Cu/Ru relay catalysis has been developed via merging the ruthenium‐catalyzed asymmetric borrowing‐hydrogen reaction with a copper‐catalyzed asymmetric Michael addition in a one‐pot procedure. The current method enables the efficient preparation of highly functionalized δ‐hydroxyesters bearing 1,4‐nonadjacent stereocenters in good yields with high levels of diastereoselectivity and excellent enantioselectivity under mild reaction conditions. The full complement of the four stereoisomers of hydroalkylation products could be readily accessed by orthogonal permutations of two chiral metal catalysts. The current work highlights the power of relay catalysis for the stereodivergent construction of 1,4‐nonadjacent stereocenters that were otherwise inaccessible. An unprecedented hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by Cu/Ru relay catalysis has been developed via merging the ruthenium-catalyzed asymmetric borrowing-hydrogen reaction with a copper-catalyzed asymmetric Michael addition in a one-pot procedure. The current method enables the efficient preparation of highly functionalized δ-hydroxyesters bearing 1,4-nonadjacent stereocenters in good yields with high levels of diastereoselectivity and excellent enantioselectivity under mild reaction conditions. The full complement of the four stereoisomers of hydroalkylation products could be readily accessed by orthogonal permutations of two chiral metal catalysts. The current work highlights the power of relay catalysis for the stereodivergent construction of 1,4-nonadjacent stereocenters that were otherwise inaccessible.An unprecedented hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by Cu/Ru relay catalysis has been developed via merging the ruthenium-catalyzed asymmetric borrowing-hydrogen reaction with a copper-catalyzed asymmetric Michael addition in a one-pot procedure. The current method enables the efficient preparation of highly functionalized δ-hydroxyesters bearing 1,4-nonadjacent stereocenters in good yields with high levels of diastereoselectivity and excellent enantioselectivity under mild reaction conditions. The full complement of the four stereoisomers of hydroalkylation products could be readily accessed by orthogonal permutations of two chiral metal catalysts. The current work highlights the power of relay catalysis for the stereodivergent construction of 1,4-nonadjacent stereocenters that were otherwise inaccessible. |
| ArticleNumber | 202206517 |
| Author | Chang, Xin Wang, Wei‐Yi Wang, Chun‐Jiang Cheng, Xiang Fu, Cong Liu, Xue‐Tao |
| Author_xml | – sequence: 1 givenname: Xin surname: Chang fullname: Chang, Xin organization: Wuhan University – sequence: 2 givenname: Xiang surname: Cheng fullname: Cheng, Xiang organization: Wuhan University – sequence: 3 givenname: Xue‐Tao surname: Liu fullname: Liu, Xue‐Tao organization: Wuhan University – sequence: 4 givenname: Cong surname: Fu fullname: Fu, Cong organization: Wuhan University – sequence: 5 givenname: Wei‐Yi surname: Wang fullname: Wang, Wei‐Yi organization: Wuhan University – sequence: 6 givenname: Chun‐Jiang orcidid: 0000-0003-3629-6889 surname: Wang fullname: Wang, Chun‐Jiang email: cjwang@whu.edu.cn organization: Nankai University |
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| Keywords | Stereodivergent ASYMMETRIC TRANSFER HYDROGENATION ENANTIOSELECTIVE FUNCTIONALIZATION Borrowing-Hydrogen Strategy BORROWING HYDROGEN ALKYLATION ALLYLATION AZOMETHINE YLIDES ALPHA-AMINO-ACIDS Stereogenic Centers METHODOLOGY COOPERATIVE CATALYSIS Relay Catalysis Asymmetric Catalysis SYNERGISTIC CU/PD CATALYSIS DUAL CATALYSIS |
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| SSID | ssj0028806 |
| Score | 2.611706 |
| Snippet | An unprecedented hydroalkylation of racemic allylic alcohols and racemic ketimine esters enabled by Cu/Ru relay catalysis has been developed via merging the... |
| Source | Web of Science |
| SourceID | proquest webofscience crossref wiley |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | e202206517 |
| SubjectTerms | Alcohols Asymmetric Catalysis Asymmetry Borrowing-Hydrogen Strategy Catalysis Catalysts Chemistry Chemistry, Multidisciplinary Copper Enantiomers Esters Permutations Physical Sciences Relay Relay Catalysis Ruthenium Science & Technology Stereodivergent Stereogenic Centers Stereoisomerism Stereoisomers Stereoselectivity |
| Title | Stereodivergent Construction of 1,4‐Nonadjacent Stereocenters via Hydroalkylation of Racemic Allylic Alcohols Enabled by Copper/Ruthenium Relay Catalysis |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.202206517 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000851324600005 https://www.proquest.com/docview/2707586678 https://www.proquest.com/docview/2681813157 |
| Volume | 61 |
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