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

Jared T. Moore; Cristian Soldi; James C. Fettinger; Jared T. Shaw

doi:10.1039/c2sc21405a

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

Jared T. Moore, Cristian Soldi, James C. Fettinger, Jared T. Shaw

Chemistry

Research output: Contribution to journal › Article › peer-review

19 Scopus citations

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	https://doi.org/10.1039/c2sc21405a
State	Published - 2013

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AU - Soldi, Cristian

AU - Fettinger, James C.

AU - Shaw, Jared T.

PY - 2013

Y1 - 2013

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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.

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

Abstract

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