Highly Enantio- and Diastereoselective Allylic Alkylation of Morita鈥揃aylis鈥揌illman Carbonates with Allyl Ketones

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• 作者：Guanghu Tong ; Bo Zhu ; Richmond Lee ; Wenguo Yang ; Davin Tan ; Caiyun Yang ; Zhiqiang Han ; Lin Yan ; Kuo-Wei Huang ; Zhiyong Jiang
• 刊名：The Journal of Organic Chemistry
• 出版年：2013
• 出版时间：May 17, 2013
• 年：2013
• 卷：78
• 期：10
• 页码：5067-5072
• 全文大小：296K
• 年卷期：v.78,no.10(May 17, 2013)
• ISSN：1520-6904

文摘

The asymmetric allylic alkylation of Morita鈥揃aylis鈥揌illman (MBH) carbonates with allyl ketones has been developed. The 伪-regioselective alkylation adducts, containing a hexa-1,5-diene framework with important synthetic value, were achieved in up to 83% yield, >99% ee, and 50:1 dr by using a commercially available Cinchona alkaloid as the catalyst. From the allylic alkylation adduct, a cyclohexene bearing two adjacent chiral centers was readily prepared.