Palladium-Catalyzed Decarboxylative Allylation/Wittig Reaction: Substrate-Controlled Synthesis of C-Vinyl Glycosides

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• 作者：Wei-Lin Leng ; Hongze Liao ; Hui Yao ; Zi-En Ang ; Shaohua Xiang ; Xue-Wei Liu
• 刊名：Organic Letters
• 出版年：2017
• 出版时间：January 20, 2017
• 年：2017
• 卷：19
• 期：2
• 页码：416-419
• 全文大小：417K
• ISSN：1523-7052

文摘

A palladium-catalyzed one-pot Tsuji–Trost type decarboxylative allylation/Wittig reaction has been developed to synthesize C-vinyl glycosides. Screening of various aldehydes led to formation of β,(E)-selective C-vinyl glycosides with pyridyl group containing aldehydes and β,(Z)-selective C-vinyl glycosides with nonpyridyl aldehydes. A plausible mechanism is proposed based on the coordination effect of the aldehydes.