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Enantioselective synthesis of functionalised tetrahydrocarbazoles via an organocatalysed Diels-Alder/ene reaction strategy

Lookup NU author(s): Joseph Cowell, Dr Ross Harrington, Professor Mike ProbertORCiD, Dr Michael HallORCiD

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Abstract

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.

Publication metadata

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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