Rh(II)-Catalyzed Enantioselective B–H Insertion of Cyclic Alkyl-Donor Carbene Generated from Diynes
Abstract
An enantioselective B-H bond insertion has been developed by employing a cyclic alkyl-donor carbene generated from diynes. Using trimethylamine borane, the reaction provides boron-substituted furan-fused dihydropiperidines bearing a carbon stereocenter, whereas 2-arylpyridine borane delivers products containing vicinal carbon/boron stereocenters with high enantioselectivity through a desymmetric B-H insertion process. This method effectively suppresses the competing 1,2-H migrations typically favored by alkyl carbenes. Furthermore, diverse transformations of the resulting B-H insertion products have been demonstrated.
Fields of Study & Subjects
Catalytic C–H Functionalization Methods
Organoboron and organosilicon chemistry
Cyclopropane Reaction Mechanisms
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 13
- Pages
- 4258–4263
- Publication date
- 23 March 2026
- Language
- EN