Journal
ACS CATALYSIS
Volume 10, Issue 19, Pages 10905-10913Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.0c03014
Keywords
heterocycles; cycloaddition; dearomatization; site selectivity; stereoselectivity
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Funding
- National Research Foundation of Korea (NRF) - Korean government [NRF-2019R1A2C1087134, NRF-2019R1A4A2001440]
- Institute for Basic Scienc in Korea [IBS-R10-D1]
- GRRC program of Gyeonggi Province [GRRCKyungHee2017-A01]
- National Research Foundation of Korea [4199990213848] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Copper-catalyzed [5 + 1] cycloadditions of N-aromatic zwitterions have been accomplished by chelation-assisted 1,2-dearomative addition of electron-deficient terminal alkynes. The unique modular skeleton of pyrazino[1,2-a]quinoline could be obtained from the regio- and stereoselective cascade annulation process, which was supported by computational studies. Further, an asymmetric variant of the developed strategy has been successfully extended for enabling access to optically enriched six-member cyclic systems.
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