Stereoselective synthesis of highly functionalized tetrahydrocarbazoles through a domino Michael–Henry reaction: an easy access to four contiguous chiral centers
摘要：
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 beta-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.
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关键词：
ENANTIOSELECTIVE NITROALDOL REACTION FRIEDEL-CRAFTS ALKYLATION DIELS-ALDER REACTIONS ALPHA-KETOPHOSPHONATES ASYMMETRIC-SYNTHESIS CASCADE REACTIONS SUBSTITUTED TETRAHYDROCARBAZOLES BIFUNCTIONAL ORGANOCATALYSTS CATALYTIC ACTIVATION
DOI：
10.1039/c3ra41409d
被引量：
年份：
2013
RSC publishing
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ResearchGate
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Royal Society of Chemistry (RSC)
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学术范
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