Preparation of Both C5鈥?Epimers of 5鈥?C-Methyladenosine: Reagent Control Trumps Substrate Control

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• 作者：Cavan M. Bligh ; Luigi Anzalone ; Young Chun Jung ; Yuegang Zhang ; William A. Nugent
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：April 4, 2014
• 年：2014
• 卷：79
• 期：7
• 页码：3238-3243
• 全文大小：276K
• 年卷期：v.79,no.7(April 4, 2014)
• ISSN：1520-6904

文摘

Adenosine-derived ketone 5 was subjected to Noyori asymmetric transfer hydrogenation (ATH) using aqueous sodium formate as a stoichiometric reductant. Despite the well-known sensitivity of ATH to stereoelectronic effects from a contiguous stereogenic center, the 5鈥?stereochemistry was overwhelmingly controlled by the chirality of the catalyst. Both the (5鈥?i>S,4鈥?i>R) and the (5鈥?i>R,4鈥?i>R) diastereomers could be prepared selectively in good yields. An efficient three-step route that provides ketone 5 in 75% overall yield was developed.