Key Laboratory of General Chemistry of the National Ethnic Affairs Commission, Key Laboratory of Pollution Control Chemistry and Environmental Functional Materials for Qinghai-Tibet Plateau of the National Ethnic Affairs Commission, School of Chemistry and Environment, Southwest Minzu University, Chengdu 610041, China.
Faculty of Geosciences and Environmental Engineering, Southwest Jiaotong University, Chengdu 610031, China.
Org Biomol Chem. 2022 Apr 20;20(16):3342-3347. doi: 10.1039/d2ob00326k.
A triple Michael/aldol cascade reaction has been established to construct tetracyclic chromanes in a diastereoselective fashion (≥5 : 1 dr). The polycyclic products were generated in 50-78% isolated yields under mild and metal-free conditions. Five reactive sites of enolate-tethered divinyl ketones were sequentially utilized to form four C-C bonds in a one-pot operation, leading to a construction of three new rings. Up to six consecutive stereocenters, including two quarternary stereogenic centers, were created in this domino process.
建立了一个三重 Michael/aldol 级联反应，以非对映选择性方式（≥5∶1 dr）构建四环色满烷。在温和且无金属条件下，多环产物以 50-78%的分离收率生成。烯醇醚化的二乙烯酮的五个反应位点被依次利用，在一锅操作中形成四个 C-C 键，导致三个新环的构建。在这个多米诺反应中，最多可以形成六个连续的立体中心，包括两个季碳立体中心。
