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Catalytic alkene cyclization reactions for the stereoselective synthesis of complex “terpenoid-like” heterocycles

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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.

Graphical abstract: Catalytic alkene cyclization reactions for the stereoselective synthesis of complex “terpenoid-like” heterocycles

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Article information


Submitted
01 Sep 2012
Accepted
25 Oct 2012
First published
25 Oct 2012

Chem. Sci., 2013,4, 292-296
Article type
Edge Article

Catalytic alkene cyclization reactions for the stereoselective synthesis of complex “terpenoid-like” heterocycles

J. T. Moore, C. Soldi, J. C. Fettinger and J. T. Shaw, Chem. Sci., 2013, 4, 292 DOI: 10.1039/C2SC21405A

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