Synthesis of trans-Cycloalkenes via Enantioselective Cyclopropanation and Skeletal Rearrangement
详细信息 查看全文
- 作者：Tomoya Miura ; Takayuki Nakamuro ; Chia-Jung Liang ; Masahiro Murakami
- 刊名：Journal of the American Chemical Society
- 出版年：2014
- 出版时间：November 12, 2014
- 年：2014
- 卷：136
- 期：45
- 页码：15905-15908
- 全文大小：338K
- ISSN：1520-5126
文摘
An efficient one-pot two-step procedure for asymmetric synthesis of piperidine-fused trans-cycloalkenes is reported. The method comprises the initial enantioselective installation of another cyclopropane ring onto methylenecyclopropanes and the subsequent thermal skeletal rearrangement in which the installed and inherent cyclopropane rings are both opened. A concerted mechanism is proposed for the latter thermal rearrangement reaction together with a closed transition state model.