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. 2023 Feb 13;62(8):e202218025.
doi: 10.1002/anie.202218025. Epub 2023 Jan 17.

Site- and Stereoselective C(sp3 )-H Borylation of Strained (Hetero)Cycloalkanols Enabled by Iridium Catalysis

Qian Gao  1   2 , Senmiao Xu  1   2
Affiliations

Site- and Stereoselective C(sp3 )-H Borylation of Strained (Hetero)Cycloalkanols Enabled by Iridium Catalysis

Qian Gao et al. Angew Chem Int Ed Engl. .

Abstract

Transition metal-catalyzed site- and stereoselective C-H activation of strained (hetero)cycloalkanes remains a formidable challenge. We herein report a carbamate-directed iridium-catalyzed asymmetric β-C(sp3 )-H borylation of cyclopropanol derivatives. A variety of densely functionalized cyclopropanols were obtained in good enantioselectivities via desymmetrization and kinetic resolution. In addition, site-selective C(sp3 )-H borylation of methine groups furnished α-borylated (hetero)cycloalkanols in moderate to good yields. The synthetic utility of the method was further shown in a gram-scale synthesis and diverse downstream transformations of borylated products.

Keywords: Asymmetric Catalysis; Chiral Bidentate Boryl Ligand; Cycloalkanols; C−H Activation; Organoboron.

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