Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/137753
Title: Addition of a carbene catalyst to indole aryl aldehyde activates a remote δ-sp2 carbon for protonation and formal [4+2] reaction
Authors: Zheng, Pengcheng
Wu, Shuquan
Mou, Chengli
Xue, Wei
Jin, Zhichao
Chi, Robin Yonggui
Keywords: Science::Chemistry::Organic chemistry
Issue Date: 2019
Source: Zheng, P., Wu, S., Mou, C., Jin, Z., & Chi, R. Y. (2019). Addition of a carbene catalyst to indole aryl aldehyde activates a remote δ-sp2 carbon for protonation and formal [4+2] reaction. Organic Letters, 21(13), 5026-5029. doi:10.1021/acs.orglett.9b01624
Journal: Organic Letters
Abstract: The addition of a carbene catalyst to an indole aryl aldehyde leads to the activation of a remote sp2 carbon that is five atoms away from the catalyst. The unsaturated Breslow intermediate formed between the catalyst and substrate undergoes an internal redox reaction and remote carbon protonation to generate an analogous azolium vinyl enolate intermediate. Subsequent [4+2] reaction with cyclic imine substrates eventually affords multicyclic pyridoindoles as nearly single diastereomers with excellent enantioselectivities.
URI: https://hdl.handle.net/10356/137753
ISSN: 1523-7060
DOI: 10.1021/acs.orglett.9b01624
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.9b01624
Fulltext Permission: open
Fulltext Availability: With Fulltext
Appears in Collections:SPMS Journal Articles

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