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 |
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ASJC Scopus subject areas
- Chemistry(all)
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Catalytic alkene cyclization reactions for the stereoselective synthesis of complex "terpenoid-like" heterocycles. / Moore, Jared T.; Soldi, Cristian; Fettinger, James C.; Shaw, Jared T.
In: Chemical Science, Vol. 4, No. 1, 2013, p. 292-296.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Catalytic alkene cyclization reactions for the stereoselective synthesis of complex "terpenoid-like" heterocycles
AU - Moore, Jared T.
AU - Soldi, Cristian
AU - Fettinger, James C.
AU - Shaw, Jared T.
PY - 2013
Y1 - 2013
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84874426938&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84874426938&partnerID=8YFLogxK
U2 - 10.1039/c2sc21405a
DO - 10.1039/c2sc21405a
M3 - Article
VL - 4
SP - 292
EP - 296
JO - Chemical Science
JF - Chemical Science
SN - 2041-6520
IS - 1
ER -