Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons
The first diastereodivergent formal [4 + 1] cycloaddition reactions of azoalkenes with p-quinone methides (p-QMs) have been accomplished. The reported reaction occurred via a domino oxa-1,4-addition/1,6-addition process, allowing the use of common azoalkenes as C1 synthons. A broad range of 2,3-di...
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| Format: | Article |
| Language: | English |
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KeAi Communications Co. Ltd.
2023-08-01
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| Series: | Green Synthesis and Catalysis |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666554922000424 |
| _version_ | 1797738969256951808 |
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| author | Chun-Yan Guan Tian-Jiao Han Shi-Kun Jia Yuan-Zhao Hua Guang-Jian Mei |
| author_facet | Chun-Yan Guan Tian-Jiao Han Shi-Kun Jia Yuan-Zhao Hua Guang-Jian Mei |
| author_sort | Chun-Yan Guan |
| collection | DOAJ |
| description | The first diastereodivergent formal [4 + 1] cycloaddition reactions of azoalkenes with p-quinone methides (p-QMs) have been accomplished. The reported reaction occurred via a domino oxa-1,4-addition/1,6-addition process, allowing the use of common azoalkenes as C1 synthons. A broad range of 2,3-dihydrobenzofurans was smoothly prepared in good yields and with reversible diastereoselectivities. The steric hindrance and hydrogen-bonding interaction were proposed to account for the two different modes of diastereo-control. The projected reaction features the employment of azoalkene as carbene-like C1 synthon, mild conditions, broad substrate scope and tunable diastereoselectivity. |
| first_indexed | 2024-03-12T13:51:30Z |
| format | Article |
| id | doaj.art-f5ada5859b6f4db9900f5f059c4b94ec |
| institution | Directory Open Access Journal |
| issn | 2666-5549 |
| language | English |
| last_indexed | 2024-03-12T13:51:30Z |
| publishDate | 2023-08-01 |
| publisher | KeAi Communications Co. Ltd. |
| record_format | Article |
| series | Green Synthesis and Catalysis |
| spelling | doaj.art-f5ada5859b6f4db9900f5f059c4b94ec2023-08-23T04:34:22ZengKeAi Communications Co. Ltd.Green Synthesis and Catalysis2666-55492023-08-0143258262Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthonsChun-Yan Guan0Tian-Jiao Han1Shi-Kun Jia2Yuan-Zhao Hua3Guang-Jian Mei4Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaGreen Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaCorresponding author.; Green Catalysis Center, College of Chemistry, Zhengzhou University, Zhengzhou 450001, ChinaThe first diastereodivergent formal [4 + 1] cycloaddition reactions of azoalkenes with p-quinone methides (p-QMs) have been accomplished. The reported reaction occurred via a domino oxa-1,4-addition/1,6-addition process, allowing the use of common azoalkenes as C1 synthons. A broad range of 2,3-dihydrobenzofurans was smoothly prepared in good yields and with reversible diastereoselectivities. The steric hindrance and hydrogen-bonding interaction were proposed to account for the two different modes of diastereo-control. The projected reaction features the employment of azoalkene as carbene-like C1 synthon, mild conditions, broad substrate scope and tunable diastereoselectivity.http://www.sciencedirect.com/science/article/pii/S2666554922000424AzoalkeneOne-carbon synthonDiastereodivergent[4 + 1] Cycloadditionpara-Quinone methides |
| spellingShingle | Chun-Yan Guan Tian-Jiao Han Shi-Kun Jia Yuan-Zhao Hua Guang-Jian Mei Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons Green Synthesis and Catalysis Azoalkene One-carbon synthon Diastereodivergent [4 + 1] Cycloaddition para-Quinone methides |
| title | Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons |
| title_full | Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons |
| title_fullStr | Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons |
| title_full_unstemmed | Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons |
| title_short | Diastereodivergent formal [4 + 1] cycloaddition of azoalkenes as one-carbon synthons |
| title_sort | diastereodivergent formal 4 1 cycloaddition of azoalkenes as one carbon synthons |
| topic | Azoalkene One-carbon synthon Diastereodivergent [4 + 1] Cycloaddition para-Quinone methides |
| url | http://www.sciencedirect.com/science/article/pii/S2666554922000424 |
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