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...
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2015
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sg-ntu-dr.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. |
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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 |
| 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. |
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School of Physical and Mathematical Sciences |
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School of Physical and Mathematical Sciences Xiang, Shaohua Hoang, Kim Le Mai He, Jingxi Tan, Yu Jia Liu, Xue-Wei |
| format |
Article |
| author |
Xiang, Shaohua Hoang, Kim Le Mai He, Jingxi Tan, Yu Jia Liu, Xue-Wei |
| author_sort |
Xiang, Shaohua |
| title |
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_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_sort |
reversing the stereoselectivity of a palladium-catalyzed o-glycosylation through an inner-sphere or outer-sphere pathway |
| publishDate |
2015 |
| 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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