Stereoelectronic factors in the stereoselective epoxidation of glycals and 4-deoxypentenosides

…, G Cheng, SK Seo, X Li, FP Boulineau…

Index: Alberch, Laura; Cheng, Gang; Seo, Seung-Kee; Li, Xuehua; Boulineau, Fabien P.; Wei, Alexander Journal of Organic Chemistry, 2011 , vol. 76, # 8 p. 2532 - 2547

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Citation Number: 28

Abstract

Glycals and 4-deoxypentenosides (4-DPs), unsaturated pyranosides with similar structures and reactivity profiles, can exhibit a high degree of stereoselectivity upon epoxidation with dimethyldioxirane (DMDO). In most cases, the glycals and their corresponding 4-DP isosteres share the same facioselectivity, implying that the pyran substituents are largely responsible for the stereodirecting effect. Fully substituted dihydropyrans are subject to a “ ...

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