Stereoselective synthesis of highly functionalized tetrahydrocarbazoles through a domino Michael–Henry reaction: an easy access to four contiguous chiral centers
- 14 May 2013
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in RSC Advances
- Vol. 3 (27) , 10644-10649
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.Keywords
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