Cy-SaBOX/Copper(II)-Catalyzed Highly Diastereo- and Enantioselective Synthesis of Bicyclic N,O Acetals
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- 作者：Qiong-Jie Liu ; Dr. Lijia Wang ; Qi-Kai Kang ; Prof. Dr. X. Peter Zhang and Prof. Dr. Yong Tang
- 刊名：Angewandte Chemie International Edition
- 出版年：2016
- 出版时间：August 1, 2016
- 年：2016
- 卷：55
- 期：32
- 页码：9220-9223
- 全文大小：710K
- ISSN：1521-3773
文摘
Facile and effective access for the asymmetric construction of the useful and important skeleton of the bicyclic N,O-acetals is described. CuII/SaBOX could catalyze the reaction of β,γ-unsaturated α-ketoesters with cyclic enamines efficiently, thus affording the desired products in excellent yields with excellent stereoselectivities (21 examples; up to 99 % yields; up to >95:5 d.r.; and 95–99 % ee). This reaction can be well performed on gram scale, even with only 1 mol % catalyst loading. The single-crystal structures of the copper complexes lead to a good understanding of the stereo-synergistic effects of the sidearm.