Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes
Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unac...
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| Published in | Journal of the American Chemical Society Vol. 141; no. 18; pp. 7637 - 7643 |
|---|---|
| Main Authors | , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
08.05.2019
Amer Chemical Soc |
| Subjects | |
| Online Access | Get full text |
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| Abstract | Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase in molecular diversity and complexity. The reaction proceeds under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids. |
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| AbstractList | Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase in molecular diversity and complexity. The reaction proceeds under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids.Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase in molecular diversity and complexity. The reaction proceeds under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids. Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase in molecular diversity and complexity. The reaction proceeds under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids. Enantioselective cross-electrophile reactions remain a challenging subject in metal catalysis, and with respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further reactions that can lead to an increase under mild conditions at room temperature, and an easily accessible chiral pyrox ligand is used to afford products with high enantioselectivity. The synthetic utility of this method is demonstrated by enabling the modification of complex molecules such as peptides, indometacin, and steroids. |
| Author | Qi, Liangliang Ma, Wei-Yuan Zhao, Zhen-Zhen Duan, Jicheng Du, Yun-Fei Su, Peifeng Tian, Zhi-Xiong Pang, Xiaobo Xu, Guang-Li Shu, Xing-Zhong Liu, Xue-Yuan Qiao, Jin-Bao |
| AuthorAffiliation | State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering |
| AuthorAffiliation_xml | – name: State Key Laboratory of Applied Organic Chemistry (SKLAOC), College of Chemistry and Chemical Engineering |
| Author_xml | – sequence: 1 givenname: Zhi-Xiong surname: Tian fullname: Tian, Zhi-Xiong – sequence: 2 givenname: Jin-Bao surname: Qiao fullname: Qiao, Jin-Bao – sequence: 3 givenname: Guang-Li surname: Xu fullname: Xu, Guang-Li – sequence: 4 givenname: Xiaobo surname: Pang fullname: Pang, Xiaobo – sequence: 5 givenname: Liangliang surname: Qi fullname: Qi, Liangliang – sequence: 6 givenname: Wei-Yuan surname: Ma fullname: Ma, Wei-Yuan – sequence: 7 givenname: Zhen-Zhen surname: Zhao fullname: Zhao, Zhen-Zhen – sequence: 8 givenname: Jicheng surname: Duan fullname: Duan, Jicheng – sequence: 9 givenname: Yun-Fei surname: Du fullname: Du, Yun-Fei – sequence: 10 givenname: Peifeng surname: Su fullname: Su, Peifeng – sequence: 11 givenname: Xue-Yuan surname: Liu fullname: Liu, Xue-Yuan – sequence: 12 givenname: Xing-Zhong orcidid: 0000-0002-0961-1508 surname: Shu fullname: Shu, Xing-Zhong email: shuxingzh@lzu.edu.cn |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/31002758$$D View this record in MEDLINE/PubMed |
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| Title | Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes |
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