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Abstract
Pd(MeCN)2Cl2 enables the alpha-stereoselective catalytic synthesis of 2,3-unsaturated O-glycosides from O(3)-acylated glycals without the requirement for additives to pre-activate either donor or nucleophile. Mechanistic studies sug-gest that, unlike traditional (η3-allyl)palladium-mediated processes, the reaction proceeds via an alkoxy-palladium inter-mediate that increases the proton acidity and oxygen nucleophilicity of the alcohol. The method is exemplified with the syn-thesis of a range of glycosides and glycoconjugates of synthetic utility.
Original language | English |
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Pages (from-to) | 2857-2860 |
Number of pages | 4 |
Journal | Organic Letters |
Volume | 19 |
Issue number | 11 |
Early online date | 12 May 2017 |
DOIs | |
Publication status | Published - 2 Jun 2017 |
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Projects
- 2 Finished