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. 2022 May 2;61(19):e202201463.
doi: 10.1002/anie.202201463. Epub 2022 Mar 14.

Iridium-Catalyzed Enantioselective C(sp3 )-H Borylation of Aminocyclopropanes

Yongjia Shi  1 , Yuhuan Yang  1 , Senmiao Xu  1   2   3
Affiliations

Iridium-Catalyzed Enantioselective C(sp3 )-H Borylation of Aminocyclopropanes

Yongjia Shi et al. Angew Chem Int Ed Engl. .

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(sp3 )-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.

Keywords: Aminocyclopropanes; Asymmetric Catalysis; Bidentate Boryl Ligands; C−H Borylation; Iridium.

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References

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