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Title: Enantioselective indole N-H functionalization enabled by addition of carbene catalyst to indole aldehyde at remote site
Authors: Yang, Xing
Luo, Guoyong
Zhou, Liejin
Liu, Bin
Zhang, Xiaolei
Gao, Hui
Jin, Zhichao
Chi, Robin Yonggui
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2019
Source: Yang, X., Luo, G., Zhou, L., Liu, B., Zhang, X., Gao, H., ... , Chi, R. Y. (2019). Enantioselective indole N-H functionalization enabled by addition of carbene catalyst to indole aldehyde at remote site. ACS Catalysis, 9(12), 10971-10976. doi:10.1021/acscatal.9b03163
Journal: ACS Catalysis
Abstract: An enantioselective functionalization of the indole NH group is developed. The reaction stereoselectivity is controlled by an N-heterocyclic carbene catalyst that adds to an aldehyde moiety at the C7-carbon of indole. The NH group participating in the carbene-catalyzed reaction is part of the heteroaromatic rings of the indole substrate. Our reactions afford multicyclic products bearing pyrroloquinazoline or oxazinoindole scaffolds widely present in bioactive molecules. Our study will encourage further exploration of carbene-catalyzed reactions of aromatic molecules and asymmetric transformation of heteroatoms in various functional molecules.
ISSN: 2155-5435
DOI: 10.1021/acscatal.9b03163
Schools: School of Physical and Mathematical Sciences 
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Catalysis, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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