Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes
Abstract The strain-release-driven reactions of bicyclo[1.1.0]butanes (BCBs) have received significant attention from chemists. Notably, 1,2-migratory reactions enabled by BCB-derived B-ate complexes effectively complement the reactions initiated by common BCBs. The desired products are particularly...
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| Format: | Article |
| Language: | English |
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Nature Portfolio
2024-12-01
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| Series: | Nature Communications |
| Online Access: | https://doi.org/10.1038/s41467-024-55161-6 |
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| author | Yu-Wen Sun Jia-Hui Zhao Xin-Yu Yan Chong-Lei Ji Huangdi Feng De-Wei Gao |
| author_facet | Yu-Wen Sun Jia-Hui Zhao Xin-Yu Yan Chong-Lei Ji Huangdi Feng De-Wei Gao |
| author_sort | Yu-Wen Sun |
| collection | DOAJ |
| description | Abstract The strain-release-driven reactions of bicyclo[1.1.0]butanes (BCBs) have received significant attention from chemists. Notably, 1,2-migratory reactions enabled by BCB-derived B-ate complexes effectively complement the reactions initiated by common BCBs. The desired products are particularly valuable for late-stage transformations due to the presence of the C–B bond. However, asymmetric reactions mediated by BCB-derived boronate complexes have progressed slowly. In this study, we develop an asymmetric synthesis of atropisomers featuring cis-cyclobutane boronic esters facilitated by 1,2-carbon or boron migration of ring-strained B-ate complexes, achieving high enantioselectivity. The reaction is compatible with various aryl, alkenyl, alkyl boronic esters and B2pin2, and shows good compatibility with natural product derivatives. Mechanistic studies are conducted to understand stereoselective control in the dynamic kinetic asymmetric transformations (DYKATs). The target products can undergo a series of transformations, further demonstrating the practicality of this methodology. |
| format | Article |
| id | doaj-art-d89da86e87cd48a0af77822f78210482 |
| institution | Kabale University |
| issn | 2041-1723 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | Nature Portfolio |
| record_format | Article |
| series | Nature Communications |
| spelling | doaj-art-d89da86e87cd48a0af77822f782104822025-01-05T12:35:09ZengNature PortfolioNature Communications2041-17232024-12-011511910.1038/s41467-024-55161-6Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexesYu-Wen Sun0Jia-Hui Zhao1Xin-Yu Yan2Chong-Lei Ji3Huangdi Feng4De-Wei Gao5School of Physical Science and Technology, ShanghaiTech UniversityCollege of Chemistry and Chemical Engineering, Shanghai University of Engineering ScienceSchool of Physical Science and Technology, ShanghaiTech UniversitySchool of Physical Science and Technology, ShanghaiTech UniversityCollege of Chemistry and Chemical Engineering, Shanghai University of Engineering ScienceSchool of Physical Science and Technology, ShanghaiTech UniversityAbstract The strain-release-driven reactions of bicyclo[1.1.0]butanes (BCBs) have received significant attention from chemists. Notably, 1,2-migratory reactions enabled by BCB-derived B-ate complexes effectively complement the reactions initiated by common BCBs. The desired products are particularly valuable for late-stage transformations due to the presence of the C–B bond. However, asymmetric reactions mediated by BCB-derived boronate complexes have progressed slowly. In this study, we develop an asymmetric synthesis of atropisomers featuring cis-cyclobutane boronic esters facilitated by 1,2-carbon or boron migration of ring-strained B-ate complexes, achieving high enantioselectivity. The reaction is compatible with various aryl, alkenyl, alkyl boronic esters and B2pin2, and shows good compatibility with natural product derivatives. Mechanistic studies are conducted to understand stereoselective control in the dynamic kinetic asymmetric transformations (DYKATs). The target products can undergo a series of transformations, further demonstrating the practicality of this methodology.https://doi.org/10.1038/s41467-024-55161-6 |
| spellingShingle | Yu-Wen Sun Jia-Hui Zhao Xin-Yu Yan Chong-Lei Ji Huangdi Feng De-Wei Gao Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes Nature Communications |
| title | Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes |
| title_full | Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes |
| title_fullStr | Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes |
| title_full_unstemmed | Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes |
| title_short | Asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring-strained B-ate complexes |
| title_sort | asymmetric synthesis of atropisomers featuring cyclobutane boronic esters facilitated by ring strained b ate complexes |
| url | https://doi.org/10.1038/s41467-024-55161-6 |
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