Litcius/Paper detail

Iridium‐Catalyzed Enantioselective C(sp<sup>3</sup>)−H Borylation of Aminocyclopropanes

Yongjia Shi, Yuhuan Yang, Senmiao Xu

2022Angewandte Chemie International Edition51 citationsDOI

Abstract

Abstract Transition‐metal‐catalyzed regio‐ and stereo‐controllable C−H functionalization remains a formidable challenge in asymmetric catalysis. Herein, we disclose the first example of iridium‐catalyzed C(sp 3 )−H borylation of aminocyclopropanes by using simple imides as weakly coordinating directing groups under mild reaction conditions. The reaction proceeded via a six‐membered iridacycle, affording a vast range of chiral aminocyclopropyl boronates. The current method features a broad spectrum of functional groups (36 examples) and high enantioselectivities (up to 99 %). We also demonstrated the synthetic utility by a preparative scale C−H borylation, C−B bond transformations, and conversion of the directing group.

Topics & Concepts

BorylationIridiumEnantioselective synthesisCatalysisChemistryCombinatorial chemistryFunctional groupOrganic chemistryArylAlkylPolymerCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsAsymmetric Hydrogenation and Catalysis