通过香豆酸酯的有机催化[4 + 3]环化反应快速构建环庚三烯
Rapid Construction of Cycloheptatriene through Organocatalyzed [4 + 3] Annulation of Coumalates.
作者信息
Zhang Haiyan, Han Xiao, Chen Tong, Wang Zhen, Yao Weijun
机构信息
School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, P. R. China.
School of Pharmaceutical Sciences and Chongqing Key Laboratory of Natural Drug Research, Chongqing University, Chongqing 401331, P. R. China.
出版信息
Org Lett. 2024 Sep 13;26(36):7495-7500. doi: 10.1021/acs.orglett.4c02179. Epub 2024 Sep 5.
A protocol for the construction of cycloheptatrienes has been developed. 4-(Dimethylamino)pyridine (DMAP) was found to be an efficient catalyst to promote the [4 + 3] annulation between coumalates and γ-alkyl-substituted allenoate or γ-aryl-3-butynoates to deliver a variety of cycloheptatrienes in moderate to good yield with excellent chemoselectivity. The asymmetric version of this annulation was also realized by using bifunctional phosphine catalyst to provide the chiral products with 32-97% ee and 29-64% yield.
已开发出一种构建环庚三烯的方案。发现4-(二甲基氨基)吡啶(DMAP)是一种有效的催化剂，可促进香豆酸酯与γ-烷基取代的烯丙酸酯或γ-芳基-3-丁炔酸酯之间的[4+3]环化反应，以中等至良好的产率和优异的化学选择性得到多种环庚三烯。通过使用双功能膦催化剂也实现了该环化反应的不对称版本，得到对映体过量值为32-97%、产率为29-64%的手性产物。
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