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Issue 27, 2013
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Stereoselective synthesis of highly functionalized tetrahydrocarbazoles through a domino Michael–Henry reaction: an easy access to four contiguous chiral centers

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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

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Supplementary files

Article information


Submitted
22 Mar 2013
Accepted
09 May 2013
First published
14 May 2013

RSC Adv., 2013,3, 10644-10649
Article type
Communication

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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