Issue 70, 2014

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

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

Supplementary files

Article information

Article type
Communication
Submitted
15 Mar 2014
Accepted
01 May 2014
First published
02 May 2014

Chem. Commun., 2014,50, 10027-10030

Author version available

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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