Asymmetric Direct 伪-Hydroxylation of 尾-Oxo Esters Catalyzed by Chiral Quaternary Ammonium Salts Derived from Cinchona Alkaloids

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• 作者：Hongjie Yao ; Mingming Lian ; Zhi Li ; Yakun Wang ; Qingwei Meng
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：November 2, 2012
• 年：2012
• 卷：77
• 期：21
• 页码：9601-9608
• 全文大小：310K
• 年卷期：v.77,no.21(November 2, 2012)
• ISSN：1520-6904

文摘

Cinchona alkaloid-derived chiral quaternary ammonium organocatalysts were developed. The catalyst with a bulky 1-adamantoyl group at the C-9 position promoted the enantioselective 伪-hydroxylation of 尾-oxo esters and resulted in the corresponding products in 35鈥?5% yields and 58鈥?0% ee. The reaction was successfully scaled to a gram-quantity scale with a similar yield without loss of enantioselectivity.