Enantioselective synthesis of bicylco[3.2.1]octan-8-ones using a tandem Michael Henry reaction
Enantioselective synthesis of bicylco[3.2.1]octan-8-ones using a tandem Michael Henry reaction
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DOI：
10.1016/j.tet.2010.04.044
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发表时间：
2010-06-19
期刊：
影响因子：
2.1
通讯作者：
Arman, Hadi
中科院分区：
文献类型：
--
作者：
Ding, Derong;Zhao, Cong-Gui;Arman, Hadi
以奎宁衍生的硫脲为催化剂，环己烷-1，2-二酮与硝基烯烃进行Michael亨利串联反应，合成了双环[3.2.1]辛-8-酮。虽然在反应过程中产生了四个立体异构中心，但仅得到两种非对映异构体，具有良好的非对映选择性和高的对映选择性（92- 99%ee）。当以3-甲基环己烷-1，2-二酮（R（1）=Me）为底物时，只得到相应热力学烯醇化物的区域异构产物。(C)2010爱思唯尔有限公司版权所有。
Bicyclo[3.2.1]octan-8-ones have been prepared from a tandem Michael Henry reaction between cyclohexane-1,2-diones and nitroalkenes using a quinine-derived thiourea as the catalyst. Although four stereogenic centers were created during the reaction, only two diastereomers were obtained in good diastereoselectivity and high enantioselectivity (92-99% ee). When 3-methylcyclohexane-1,2-dione (R(1)=Me) was used as the substrate, only the regioisomeric product of the corresponding thermodynamic enolate was obtained. (C) 2010 Elsevier Ltd. All rights reserved.