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Issue 70, 2014
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One-pot enantioselective construction of indoloquinolizidine derivatives bearing five contiguous stereocenters using aliphatic aldehydes, nitroethylenes, and tryptamine

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Abstract

An organocatalytic cascade reaction was established for the construction of indoloquinolizidine derivatives bearing five contiguous stereocenters from readily available aliphatic aldehydes, nitroethylenes, and tryptamine. This one-pot process gave 30–55% overall yields with excellent d.r. (>20 : 1 in all cases) and ee (91–98%). Additionally, quaternary stereogenic carbon center-containing indoloquinolizidines were prepared through NBS-mediated cyclization of one of the intermediates.

Graphical abstract: One-pot enantioselective construction of indoloquinolizidine derivatives bearing five contiguous stereocenters using aliphatic aldehydes, nitroethylenes, and tryptamine

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Publication details

The article was received on 15 Mar 2014, accepted on 01 May 2014 and first published on 02 May 2014


Article type: Communication
DOI: 10.1039/C4CC01929F
Citation: Chem. Commun., 2014,50, 10027-10030
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    One-pot enantioselective construction of indoloquinolizidine derivatives bearing five contiguous stereocenters using aliphatic aldehydes, nitroethylenes, and tryptamine

    Y. Tan, H. Luan, H. Lin, X. Sun, X. Yang, H. Dong and G. Lin, Chem. Commun., 2014, 50, 10027
    DOI: 10.1039/C4CC01929F

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