Synthesis of Chiral [2.2]Paracyclophane-Derived Chromenoisoxazolidines Bearing Multiple Stereocenters
Wei-Kang Jiao1, Xue-Bai Wei1, Yu-Nan Zhu1
1Key Laboratory of Chemistry and Engineering of Forest Products, State Ethnic Affairs Commission; Guangxi Key Laboratory of Chemistry and Engineering of Forest Products; Engineering Research Center of Low-Carbon and High-Quality Utilization of Forest Biomass, University of Guangxi; School of Chemistry and Chemical Engineering, Guangxi Minzu University, Nanning 530006, China.
Abstract:
A series of chiral [2.2]paracyclophane(pCp)-derived chromenoisoxazolidines bearing multiple stereocenters were synthesized in good to excellent yields (42%-99%), high diastereoselectivity (>10:1), and excellent enantioselectivity (98.2%-99.9%) through a Yb(OTf)3-catalyzed condensation/(3 + 2) cycloaddition cascade strategy in a one-pot reaction from pCp-derived O-allylated aldehydes and substituted hydroxylamines under mild conditions. Mechanistic studies showed that the planar chirality of paracyclophane scaffold could control the diastereoselectivity of (3 + 2) cycloaddition. The present method features a broad substrate scope, good functional group tolerance, C-C/C-N/C-O bonds and two ring formations in a single operation, high diastereoselectivity and enantioselectivity of multiple stereocenters, and diverse novel paracyclophane derivatives.
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