Rhodium-catalysed selective C–C bond activation and borylation of cyclopropanes
Yandong Wang, Jingyi Bai, Youqing Yang, Wenxuan Zhao, Yong Liang, Di Wang, Yue Zhao, Zhuangzhi Shi
Abstract
-Piv-substituted cyclopropylamines (CPAs) undergo proximal-selective hydroboration with HBpin to provide valuable γ-amino boronates in one step which are otherwise difficult to synthesize by known methods. The enantioenriched substrates can deliver chiral products without erosion of the enantioselectivities. Versatile synthetic utility of the obtained γ-amino boronates is also demonstrated. Experimental and computational mechanistic studies showed the preferred pathway and the origin of this selectivity. This study will enable the further use of CPAs as valuable building blocks for the tunable generation of C-heteroatom or C-C bonds through selective C-C bond activation.