Asymmetric H2O-Nucleophilic Ring Opening of D鈥揂 Cyclopropanes: Catalyst Serves as a Source of Water

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• 作者：Qi-Kai Kang ; Lijia Wang ; Qiong-Jie Liu ; Jun-Fang Li ; Yong Tang
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：November 25, 2015
• 年：2015
• 卷：137
• 期：46
• 页码：14594-14597
• 全文大小：465K
• ISSN：1520-5126

文摘

The first catalytic enantioselective ring-opening reaction of donor鈥揳cceptor cyclopropanes with water is described. By employing Cy-TOX/Cu(II) as catalyst, the reaction performed very well over a broad range of substrates, leading to the ring-opening products in 70鈥?6% yields with up to 95% ee under mild conditions. The current method provides a new approach to direct access to 纬-substituted GBH derivatives very efficiently. Importantly, Cu(ClO₄)₂路6H₂O proves to serve as both a Lewis acid and a source of water, which affords a fine system to controllably release water as a nucleophile in the asymmetric catalysis.