Pd‐Catalyzed Asymmetric Allylation of an o‐Carborane Derivative.

Lebedev, R. V.; Moiseev, S. K.; Bondarev, Oleg G.; Il’in, M. M.; Gavrilov, K. N.; Калинин, В. Н.

doi:10.1002/chin.200239178

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2023

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“…for o-carborane derivatives bearing chirality on C-proximity by Pd-catalyzed allylation reaction in the presence of chiral ligand (Fig. 1c) 25 . If the substituents on the cage carbon atoms are different, substitution at B(3) position provides a pair of enantiomer possessing chiral center on the plane.…”

Section: Introductionmentioning

confidence: 99%

Site- and enantioselective B−H functionalization of carboranes

Lee,

González-Montiel

et al. 2023

Preprint

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Functionalization of carboranes, icosahedral boron − carbon molecular clusters, is of great interest as they have wide applications in medicinal and materials chemistry. Thus, site- and enantioselective synthesis of carboranes requires complete control of the reaction. Herein, we describe the first asymmetric Rh(II)-catalyzed insertion reactions of carbenes into cage B − H bond of carboranes. This reaction thereby generates carboranes possessing a carbon-stereocenter adjacent to cage boron of the carborane, in excellent site- and enantioselectivity under mild reaction conditions. The first fully computed transition structures of Rh(II)-catalyzed carbene insertion process through density functional theory are reported. These B − H insertion transition structures, in conjunction with newly employed topographical proximity surfaces analyses, visually reveal the region between the carborane and the phthalimide ligands responsible for the selectivities of this reaction.

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Section: Introductionmentioning

confidence: 99%