Atroposelective Synthesis of C-N Vinylindole Atropisomers by Palladium-Catalyzed Asymmetric Hydroarylation of 1-Alkynylindoles.

Autor: Zhan LW; College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071, China., Lu CJ; College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071, China., Feng J; College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071, China., Liu RR; College of Chemistry and Chemical Engineering, Qingdao University, Ningxia Road 308#, Qingdao, 266071, China.
Jazyk: angličtina
Zdroj: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2023 Nov 06; Vol. 62 (45), pp. e202312930. Date of Electronic Publication: 2023 Oct 06.
DOI: 10.1002/anie.202312930
Abstrakt: Transition-metal-catalyzed hydroarylation of unsymmetrical internal alkynes remains challenging because of the difficulty in controlling regioselectivity and stereoselectivity. Moreover, the enantioselective hydroarylation of alkynes using organoboron reagents has not been reported. Herein, we report for the first time that palladium compounds can catalyze the hydroarylation of 1-alkynylindoles with organoborons for the synthesis of chiral C-N atropisomers. A series of rarely reported vinylindole atropisomers was synthesized with excellent regio-, stereo- (Z-selectivity), and enantioselectivity under mild reaction conditions. The ready availability of organoborons and alkynes and the simplicity, high stereoselectivity, and good functional group tolerance of this catalytic system make it highly attractive.
(© 2023 Wiley-VCH GmbH.)
Databáze: MEDLINE
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