Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins
Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins have been developed to afford chiral dispiro[indene-pyrrolidine-pyrimidine]s. Through this strategy, the target products could be obtained in good to excellent yield...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.3 |
| _version_ | 1828438182381748224 |
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| author | Jiang-Song Zhai Da-Ming Du |
| author_facet | Jiang-Song Zhai Da-Ming Du |
| author_sort | Jiang-Song Zhai |
| collection | DOAJ |
| description | Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins have been developed to afford chiral dispiro[indene-pyrrolidine-pyrimidine]s. Through this strategy, the target products could be obtained in good to excellent yields with excellent stereoselectivities. In addition, the synthetic utility was verified through a gram-scale synthesis, one-pot three-component reactions and further transformation experiments of the products. |
| first_indexed | 2024-12-10T20:00:44Z |
| format | Article |
| id | doaj.art-0535f4343af243d885e732ab273dceac |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-10T20:00:44Z |
| publishDate | 2022-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-0535f4343af243d885e732ab273dceac2022-12-22T01:35:32ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-01-01181253610.3762/bjoc.18.31860-5397-18-3Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefinsJiang-Song Zhai0Da-Ming Du1School of Chemistry and Chemical Engineering, Beijing Institute of Technology, No.5 Zhongguancun South Street, Beijing 100081, People’s Republic of ChinaSchool of Chemistry and Chemical Engineering, Beijing Institute of Technology, No.5 Zhongguancun South Street, Beijing 100081, People’s Republic of ChinaBifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins have been developed to afford chiral dispiro[indene-pyrrolidine-pyrimidine]s. Through this strategy, the target products could be obtained in good to excellent yields with excellent stereoselectivities. In addition, the synthetic utility was verified through a gram-scale synthesis, one-pot three-component reactions and further transformation experiments of the products.https://doi.org/10.3762/bjoc.18.3asymmetric catalysiscyclization reactionmichael additionone-pot three-component reactionspirobarbiturates |
| spellingShingle | Jiang-Song Zhai Da-Ming Du Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins Beilstein Journal of Organic Chemistry asymmetric catalysis cyclization reaction michael addition one-pot three-component reaction spirobarbiturates |
| title | Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins |
| title_full | Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins |
| title_fullStr | Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins |
| title_full_unstemmed | Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins |
| title_short | Bifunctional thiourea-catalyzed asymmetric [3 + 2] annulation reactions of 2-isothiocyanato-1-indanones with barbiturate-based olefins |
| title_sort | bifunctional thiourea catalyzed asymmetric 3 2 annulation reactions of 2 isothiocyanato 1 indanones with barbiturate based olefins |
| topic | asymmetric catalysis cyclization reaction michael addition one-pot three-component reaction spirobarbiturates |
| url | https://doi.org/10.3762/bjoc.18.3 |
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