Lewis Base Catalyzed Enantioselective Allylic Hydroxylation of Morita鈥揃aylis鈥揌illman Carbonates with Water

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• 作者：Bo Zhu ; Lin Yan ; Yuanhang Pan ; Richmond Lee ; Hongjun Liu ; Zhiqiang Han ; Kuo-Wei Huang ; Choon-Hong Tan ; Zhiyong Jiang
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：August 19, 2011
• 年：2011
• 卷：76
• 期：16
• 页码：6894-6900
• 全文大小：894K
• 年卷期：v.76,no.16(August 19, 2011)
• ISSN：1520-6904

文摘

A Lewis base catalyzed allylic hydroxylation of Morita鈥揃aylis鈥揌illman (MBH) carbonates has been developed. Various chiral MBH alcohols can be synthesized in high yields (up to 99%) and excellent enantioselectivities (up to 94% ee). This is the first report using water as a nucleophile in asymmetric organocatalysis. The nucleophilic role of water has been verified using ¹⁸O-labeling experiments.