Copper-Catalyzed Intramolecular Desymmetric Aryl CO Coupling for the Enantioselective Construction of Chiral Dihydrobenzofurans and Dihydrobenzopyrans
O‐Heterocyclic structures such as 2,3‐dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine. A broad ran...
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| Published in | Angewandte Chemie International Edition Vol. 54; no. 30; pp. 8805 - 8808 |
|---|---|
| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
20.07.2015
WILEY‐VCH Verlag |
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| Abstract | O‐Heterocyclic structures such as 2,3‐dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine. A broad range of substrates are compatible with this CuI‐diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions.
O‐Heterocyclic structures such as chiral dihydrobenzofurans can be formed enantioselectively through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine ligand. A broad range of substrates is compatible with this CuI‐diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions. |
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| AbstractList | O-Heterocyclic structures such as 2,3-dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper-catalyzed desymmetrization strategy with a chiral cyclic 1,2-diamine. A broad range of substrates are compatible with this Cu super(I)-diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions. O-Heterocyclic structures such as chiral dihydrobenzofurans can be formed enantioselectively through a copper-catalyzed desymmetrization strategy with a chiral cyclic 1,2-diamine ligand. A broad range of substrates is compatible with this Cu super(I)-diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions. O‐Heterocyclic structures such as 2,3‐dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine. A broad range of substrates are compatible with this Cu I ‐diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions. O‐Heterocyclic structures such as 2,3‐dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine. A broad range of substrates are compatible with this CuI‐diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions. O‐Heterocyclic structures such as chiral dihydrobenzofurans can be formed enantioselectively through a copper‐catalyzed desymmetrization strategy with a chiral cyclic 1,2‐diamine ligand. A broad range of substrates is compatible with this CuI‐diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions. O-Heterocyclic structures such as 2,3-dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral dihydrobenzofurans and analogues was achieved through a copper-catalyzed desymmetrization strategy with a chiral cyclic 1,2-diamine. A broad range of substrates are compatible with this Cu(I)-diamine catalytic system and afford the desired coupling products with chiral tertiary or quaternary carbon centers in high yields and good to excellent enantioselectivities under mild conditions. |
| Author | Liu, Yangyuan Cai, Qian Yang, Wenqiang Zhang, Shasha |
| Author_xml | – sequence: 1 givenname: Wenqiang surname: Yang fullname: Yang, Wenqiang organization: Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No.190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou, 510530 (China) – sequence: 2 givenname: Yangyuan surname: Liu fullname: Liu, Yangyuan organization: College of Chemistry and Chemical Engineering, Hunan Normal University, No. 36 Lushan Road, Changsha, 410081 (China) – sequence: 3 givenname: Shasha surname: Zhang fullname: Zhang, Shasha organization: Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No.190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou, 510530 (China) – sequence: 4 givenname: Qian surname: Cai fullname: Cai, Qian email: cai_qian@gibh.ac.cn organization: Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No.190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou, 510530 (China) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/26060986$$D View this record in MEDLINE/PubMed |
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| Copyright | 2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
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| Keywords | O-arylation copper 2,3-dihydrobenzofuran desymmetrization asymmetric catalysis |
| Language | English |
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| Notes | ark:/67375/WNG-NFTQJT5B-8 We are grateful to the National Natural Science Foundation (Grant 21272234) for their financial support. We also thank Prof. Dr. Jinsong Liu and Yongzhi Lu from Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, for the X-ray experiments. istex:249AF05A9CA83663506932CE605AC2E013D36579 National Natural Science Foundation - No. 21272234 ArticleID:ANIE201503882 We are grateful to the National Natural Science Foundation (Grant 21272234) for their financial support. We also thank Prof. Dr. Jinsong Liu and Yongzhi Lu from Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, for the X‐ray experiments. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| Snippet | O‐Heterocyclic structures such as 2,3‐dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral... O-Heterocyclic structures such as 2,3-dihydrobenzofurans are key motifs in many natural compounds and pharmaceuticals. Enantioselective formation of chiral... |
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| SubjectTerms | 2,3‐dihydrobenzofuran 3-dihydrobenzofuran Aromatic compounds asymmetric catalysis Benzofurans - chemical synthesis Benzofurans - chemistry Carbon Catalysis Catalysts Chromans - chemical synthesis Chromans - chemistry Compatibility copper Copper - chemistry desymmetrization Joining Ligands O-arylation Stereoisomerism Strategy |
| Title | Copper-Catalyzed Intramolecular Desymmetric Aryl CO Coupling for the Enantioselective Construction of Chiral Dihydrobenzofurans and Dihydrobenzopyrans |
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