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Lookup NU author(s): Joseph Cowell, Dr Ross Harrington, Professor Mike ProbertORCiD, Dr Michael HallORCiD
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License (CC BY-NC-ND).
Functionalised tetrahydrocarbazoles are accessed through an enantioselective organocatalysed Diels-Alder (D-A) reaction of 3-vinyl-1H-indole with a suitable dienophile in combination with an in situ N-protection. A subsequent diastereospecific ene reaction is then used to transfer chirality from the 10a to the 5 position with rearomatisation of the indolic ring, to give the target tetrahydrocarbazoles in high %ee. The in situ introduction of different N-protecting groups is explored along with their influence on the subsequent ene reactions.
Author(s): Cowell J, Harrington RW, Probert MR, Hall MJ
Publication type: Article
Publication status: Published
Journal: Tetrahedron: Asymmetry
Year: 2015
Volume: 26
Issue: 20
Pages: 1189-1196
Print publication date: 01/11/2015
Online publication date: 29/09/2015
Acceptance date: 04/09/2015
Date deposited: 11/11/2015
ISSN (print): 0957-4166
ISSN (electronic): 1362-511X
Publisher: Pergamon Press
URL: http://dx.doi.org/10.1016/j.tetasy.2015.09.004
DOI: 10.1016/j.tetasy.2015.09.004
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