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Rh(II)-Catalyzed Enantioselective B-H Insertion of Cyclic Alkyl-Donor Carbene Generated from Diynes
Shunlong Liu1, Rui Wu2, Shifa Zhu1,2
1Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, 510640, P. R. China.
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.
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