Enantioselective Construction of Vicinal Diaxial Styrenes and Multiaxis System via Organocatalysis

A highly diastereo- and enantioselective
methodology for the asymmetric
synthesis of vicinal diaxial styrenes and multiaxis system was achieved
by organocatalysis. Various vicinal diaxial styrenes and multiaxis
systems were obtained in excellent enantioselective manners. The mechanism
studies revealed that a new tetra-substituted vinylidene ortho-quinone methide (VQM) intermediate was likely involved
and accounted for the excellent enantioselectivity.

本研究通过有机催化（organocatalysis）构建了一种兼具高非对映选择性与对映选择性的不对称合成方法，可用于邻位双轴向苯乙烯类化合物与多轴体系的不对称合成。多种邻位双轴向苯乙烯类化合物及多轴体系均能以优异的对映选择性得到合成。机理研究显示，反应中可能涉及一种新型四取代亚乙烯基邻亚甲基醌（VQM）中间体，该中间体正是实现优异对映选择性的关键因素。