Abstract
A new catalytic synthesis of densely substituted tetrahydroquinolines is described. This reaction forms up to two rings, three bonds, and three stereogenic centers with excellent stereo- and regiocontrol in a single step. Although control experiments demonstrate that the active catalyst is protic acid, Sc(OTf)3 serves as an effective and practical pre-catalyst. The scope of this reaction is demonstrated with 21 monocyclizations and 14 bicyclization reactions.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 292-296 |
| Number of pages | 5 |
| Journal | Chemical Science |
| Volume | 4 |
| Issue number | 1 |
| DOIs | |
| State | Published - 2013 |
ASJC Scopus subject areas
- Chemistry(all)
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Moore, J. T., Soldi, C., Fettinger, J. C., & Shaw, J. T. (2013). Catalytic alkene cyclization reactions for the stereoselective synthesis of complex "terpenoid-like" heterocycles. Chemical Science, 4(1), 292-296. https://doi.org/10.1039/c2sc21405a