Stereoselective Desymmetrization of gem-Diborylalkanes by “Trifluorination”

Citation:

Kumar, N. ; Reddy, R. R. ; Masarwa*, A. Stereoselective Desymmetrization of gem-Diborylalkanes by “Trifluorination”. Chemistry – A European Journal 2019, 25, 8008-8012.

Abstract:

An efficient and general method for the chemoselective synthesis of unsymmetrical gem-diborylalkanes is reported. This method is based on a novel late-stage desymmetrization via nucleophilic “trifluorination”, providing chiral gem-diborylalkanes bearing a trifluoroborate group. The reaction offers a highly modular and diastereoselective approach to synthesize gem-diborylcyclopropanes. The utility of the gem-diborylalkane building blocks was demonstrated by selective post-functionalization of the trifluoroborate group. These functionalizations include inter- and intra- Pd-catalyzed Suzuki−Miyaura coupling reactions.

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Last updated on 02/28/2023