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

ASJC Scopus subject areas

  • Chemistry(all)

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