Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway
An efficient and concise method for the construction of various O-glycosidic bonds by a palladium-catalyzed reaction with a 3-O-picoloyl glucal has been developed. The stereochemistry of the anomeric center derives from either an inner-sphere or outer-sphere pathway. Harder nucleophiles, such as ali...
| Main Authors: | , , , , |
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| Other Authors: | |
| Format: | Journal Article |
| Language: | English |
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2015
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| Online Access: | https://hdl.handle.net/10356/106703 http://hdl.handle.net/10220/25100 http://dx.doi.org/10.1002/anie.201408739 |
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| author | Xiang, Shaohua Hoang, Kim Le Mai He, Jingxi Tan, Yu Jia Liu, Xue-Wei |
| author2 | School of Physical and Mathematical Sciences |
| author_facet | School of Physical and Mathematical Sciences Xiang, Shaohua Hoang, Kim Le Mai He, Jingxi Tan, Yu Jia Liu, Xue-Wei |
| author_sort | Xiang, Shaohua |
| collection | NTU |
| description | An efficient and concise method for the construction of various O-glycosidic bonds by a palladium-catalyzed reaction with a 3-O-picoloyl glucal has been developed. The stereochemistry of the anomeric center derives from either an inner-sphere or outer-sphere pathway. Harder nucleophiles, such as aliphatic alcohols and sodium phenoxides give β-products, and α products result from using softer nucleophiles, such as phenol. |
| first_indexed | 2025-02-19T03:17:06Z |
| format | Journal Article |
| id | ntu-10356/106703 |
| institution | Nanyang Technological University |
| language | English |
| last_indexed | 2025-02-19T03:17:06Z |
| publishDate | 2015 |
| record_format | dspace |
| spelling | ntu-10356/1067032019-12-06T22:16:30Z Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway Xiang, Shaohua Hoang, Kim Le Mai He, Jingxi Tan, Yu Jia Liu, Xue-Wei School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Physical chemistry::Stereochemistry An efficient and concise method for the construction of various O-glycosidic bonds by a palladium-catalyzed reaction with a 3-O-picoloyl glucal has been developed. The stereochemistry of the anomeric center derives from either an inner-sphere or outer-sphere pathway. Harder nucleophiles, such as aliphatic alcohols and sodium phenoxides give β-products, and α products result from using softer nucleophiles, such as phenol. 2015-02-26T02:03:04Z 2019-12-06T22:16:30Z 2015-02-26T02:03:04Z 2019-12-06T22:16:30Z 2015 2015 Journal Article Xiang, S., Hoang, K. L. M., He, J., Tan, Y. J., & Liu, X.-W. (2015). Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway. Angewandte chemie International edition, 54(2), 604-607. 1433-7851 https://hdl.handle.net/10356/106703 http://hdl.handle.net/10220/25100 http://dx.doi.org/10.1002/anie.201408739 en Angewandte chemie International edition © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| spellingShingle | DRNTU::Science::Chemistry::Physical chemistry::Stereochemistry Xiang, Shaohua Hoang, Kim Le Mai He, Jingxi Tan, Yu Jia Liu, Xue-Wei Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway |
| title | Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway |
| title_full | Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway |
| title_fullStr | Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway |
| title_full_unstemmed | Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway |
| title_short | Reversing the stereoselectivity of a palladium-catalyzed O-glycosylation through an inner-sphere or outer-sphere pathway |
| title_sort | reversing the stereoselectivity of a palladium catalyzed o glycosylation through an inner sphere or outer sphere pathway |
| topic | DRNTU::Science::Chemistry::Physical chemistry::Stereochemistry |
| url | https://hdl.handle.net/10356/106703 http://hdl.handle.net/10220/25100 http://dx.doi.org/10.1002/anie.201408739 |
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