Jump to main content
Jump to site search

Issue 27, 2013
Previous Article Next Article

Stereoselective synthesis of highly functionalized tetrahydrocarbazoles through a domino Michael–Henry reaction: an easy access to four contiguous chiral centers

Author affiliations

Abstract

For the first time, a very simple, efficient, mild, catalytic and one-step procedure for the synthesis of a series of densely functionalized 1-methoxycarbonyl-2-aryl-3-nitro-4-hydroxy-1,2,3,4-tetrahydro-9H-carbazole derivatives has been achieved via a domino Michael–Henry reaction of methyl 3-formyl-1H-indole-2-acetates with β-nitrostyrenes using DABCO as an organocatalyst. Furthermore, the high enantio-(≤92% ee) and diastereoselective (≤12 : 1 dr) synthesis of the title compounds has been achieved with excellent yields using 9-O-benzylcupreidine (10 mol%) as a catalyst.

Graphical abstract: Stereoselective synthesis of highly functionalized tetrahydrocarbazoles through a domino Michael–Henry reaction: an easy access to four contiguous chiral centers

Back to tab navigation

Supplementary files

Publication details

The article was received on 22 Mar 2013, accepted on 09 May 2013 and first published on 14 May 2013


Article type: Communication
DOI: 10.1039/C3RA41409D
Citation: RSC Adv., 2013,3, 10644-10649
  •   Request permissions

    Stereoselective synthesis of highly functionalized tetrahydrocarbazoles through a domino Michael–Henry reaction: an easy access to four contiguous chiral centers

    P. K. Jaiswal, S. Biswas, S. Singh, B. Pathak, S. M. Mobin and S. Samanta, RSC Adv., 2013, 3, 10644
    DOI: 10.1039/C3RA41409D

Search articles by author

Spotlight

Advertisements