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

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

Research output: Contribution to journalArticle

17 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)292-296
Number of pages5
JournalChemical Science
Volume4
Issue number1
DOIs
StatePublished - 2013

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Cyclization
Terpenes
Alkenes
Catalysts
Acids
Experiments
scandium triflate
1,2,3,4-tetrahydroquinoline

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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 journalArticle

Moore, Jared T. ; Soldi, Cristian ; Fettinger, James C. ; Shaw, Jared T. / Catalytic alkene cyclization reactions for the stereoselective synthesis of complex "terpenoid-like" heterocycles. In: Chemical Science. 2013 ; Vol. 4, No. 1. pp. 292-296.
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