Issue 27, 2013

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

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

Supplementary files

Article information

Article type
Communication
Submitted
22 Mar 2013
Accepted
09 May 2013
First published
14 May 2013

RSC Adv., 2013,3, 10644-10649

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

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