Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles
Name
RLD BAN Indole Text 8-15.pdf
Size
1 MB
Format
Adobe PDF
Checksum (MD5)
b29c8c906776e9af9e0ec356d36ef2ee
Author(s)
Lam, Tin Yiu
Wang, Yu-Pu
Danheiser, Rick Lane
Date Issued
September 2013
Journal
Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Lam, Tin Yiu, Yu-Pu Wang, and Rick L. Danheiser. “Benzannulation via the Reaction of Ynamides and Vinylketenes. Application to the Synthesis of Highly Substituted Indoles.” The Journal of Organic Chemistry 78, no. 18 (September 20, 2013): 9396–9414.
Version
Author's final manuscript
Abstract
A two-stage “tandem strategy” for the synthesis of indoles with a high level of substitution on the six-membered ring is described. Benzannulation based on the reaction of cyclobutenones with ynamides proceeds via a cascade of four pericyclic reactions to produce multiply substituted aniline derivatives in which the position ortho to the nitrogen can bear a wide range of functionalized substituents. In the second stage of the tandem strategy, highly substituted indoles are generated via acid-, base-, and palladium-catalyzed cyclization and annulation processes.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
Terms of Use
Article is made available in accordance with the publisher's policy and may be subject to US copyright law. Please refer to the publisher's site for terms of use.
Persistent DSpace Link
DOI of Published Version
https://doi.org/10.1021/jo401635c
