Journal
ORGANIC LETTERS
Volume 21, Issue 9, Pages 3067-3071Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.9b00652
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Funding
- DST-SERB [EMR/2016/003677]
- CSIR, New Delhi
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An efficient tandem rhodium(II)/squaramide relay catalysis of readily accessible indole derivatives and N-sulfonyl-1,2,3-triazoles has been developed for the enantioselective synthesis of dihydro-beta-carbolines in good yield and enantioselectivity. The developed reaction involves selective insertion of in situ generated azavinyl rhodium carbene onto the C3-H bond of indole derivatives and subsequent squaramide-catalyzed enantioselective intramolecular aza-Michael reaction. Furthermore, the potential of the strategy was demonstrated through the ready conversion to potent tetrahydro-beta-carbolines and the tetracyclic alkaloid core structure.
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