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Abstract Chiral N-heterocyclic organoboronates represent promising intermediates for the preparation of various bioactive and pharmaceutical compounds. We recently reported the first asymmetric dearomative borylation of indoles by copper-catalyzed borylation. Then… Click to show full abstract
Abstract Chiral N-heterocyclic organoboronates represent promising intermediates for the preparation of various bioactive and pharmaceutical compounds. We recently reported the first asymmetric dearomative borylation of indoles by copper-catalyzed borylation. Then we further developed dearomatization/enantioselective borylation sequence. Chiral 3-boryl-tetrahydropyridines and chiral boryl-tetrahydroquinolines via the copper(I)-catalyzed regio-, diastereo- and enantioselective borylation of 1,2-dihydropyridines and 1,2-dihydroquinilines, which were prepared by the partial reduction of the corresponding pyridine or quinoline derivatives. This dearomatization/enantioselective borylation procedures provide a direct access to chiral piperidines and tetrahydroquinolines from readily available pyridines or quinolines in combination with the stereospecific transformation of the stereogenic C–B bond.
Journal Title: Pure and Applied Chemistry
Year Published: 2018
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