Jump to main content
Jump to site search

Issue 16, 2018
Previous Article Next Article

Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles

Author affiliations

Abstract

Direct and expedient access to densely substituted tetrahydrocarbazoles and tetrahydrocycloheptadiindoles bearing multiple contiguous stereocentres has been achieved via a two-fold divergent diastereoselective (dr up to >99 : 1) transformation of 2-vinylindoles. The high-yielding conversions (yield up to 87%) that are amenable for a wide range of substituted 2-vinylindoles proceed through Lewis acid-catalyzed [4 + 2] and [4 + 3] cyclization–aromatization cascade reactions, respectively, involving a heretofore-unprecedented reversal of the polarity (umpolung) of 2-vinylindoles. The two synthetic routes are effortlessly transposable into each other by merely modulating the temperature to furnish the corresponding products in a selective and exclusive fashion. In addition, another novel synthetic route to tetrahydroindolocarbazoles has been developed that advances via a formal [4 + 2] cyclization of 4-vinylindoles involving sequential C3 Michael addition–dearomatization–aromatization cascade reactions.

Graphical abstract: Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles

Back to tab navigation

Supplementary files

Publication details

The article was received on 27 Jan 2018, accepted on 22 Mar 2018 and first published on 22 Mar 2018


Article type: Paper
DOI: 10.1039/C8OB00228B
Citation: Org. Biomol. Chem., 2018,16, 2910-2922
  •   Request permissions

    Temperature-modulated diastereoselective transformations of 2-vinylindoles to tetrahydrocarbazoles and tetrahydrocycloheptadiindoles

    I. A. Wani, A. Bhattacharyya, M. Sayyad and M. K. Ghorai, Org. Biomol. Chem., 2018, 16, 2910
    DOI: 10.1039/C8OB00228B

Search articles by author

Spotlight

Advertisements