Catalytic Atroposelective Synthesis of N–N Axially Chiral Indolylamides
Tian‐Zhen Li, Shufang Wu, Ning‐Yi Wang, Chen-Shengping Hong, Yu‐Chen Zhang, Feng Shi
Abstract
High Resolution Image Download MS PowerPoint Slide The catalytic atroposelective synthesis of N–N axially chiral indolylamides was established via dynamic kinetic resolution, which makes use of chiral Lewis base-catalyzed asymmetric acylation of N -acylaminoindoles as a new type of platform molecule with anhydrides. By this strategy, a series of N–N axially chiral indolylamides were synthesized in overall good yields (up to 98%) with excellent enantioselectivities (up to 99% ee). Moreover, some of these N–N axially chiral indolylamides display some extent of anticancer activity, which demonstrates their potential application in medicinal chemistry. Therefore, this work has not only provided a new strategy for the synthesis of N–N axially chiral monoaryl indoles but also offered a new member of N–N axially chiral monoaryl indoles with configurational stability and promising application, thereby solving the challenges in atroposelective synthesis and application of N–N axially chiral monoaryl indoles.