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Cobalt-Catalyzed Asymmetric Construction of Boron Stereocenters With C–N Axial Chirality
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DOI：10.1002/advs.77047.png)
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Abstract
En 中文
The efficient construction of boron stereogenic centers alongside axial chirality remains a significant synthetic challenge, particularly under one-pot conditions. Herein, we report a cobalt/Salox-catalyzed enantioselective annulation strategy that enables the simultaneous formation of B-stereogenic frameworks and a C─N chiral axis via C─H and N─H annulation of arylamides with dialkynylborons. This protocol achieves asymmetric desymmetrization at boron along with effective diastereocontrol on the C─N axis under mild conditions. A wide range of aryl amides and alkynes are well tolerated, delivering structurally diverse products in good yields with consistently high diastereo- and enantioselectivities. Mechanistic studies, including control experiments and isotope labelling, provide insight into the reaction pathway and the origin of stereocontrol. The resulting chiral boron-containing compounds exhibit notable fluorescence, and their photophysical properties suggest potential utility in optoelectronic applications.
Keywords:
asymmetric catalysis
atropisomers
boron
cobalt
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