Organocatalytic asymmetric arylative dearomatization of 2,3-disubstituted indoles enabled by tandem reactions
Yu-Chen Zhang1, Jia-Jia Zhao, Fei Jiang
1School of Chemistry and Chemical Engineering, Jiangsu Normal University, Xuzhou, 221116 (China).
Abstract:
The organocatalytic asymmetric arylative dearomatization of indoles was achieved through two tandem approaches involving 2,3-disubstituted indoles and quinone imine ketals. One approach utilized the enantioselective cascade 1,4 addition/alcohol elimination reaction, the other employed the one-pot tandem arylative dearomatization/transfer hydrogenation sequence. In both cases, enantiomerically pure indole derivatives that bear an all-carbon quaternary stereogenic center were generated in high yields and excellent stereoselectivities (all d.r.>95:5, up to 99% ee).
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