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Catalytic Alkene Cyclization Reactions for the Stereoselective Synthesis of Complex "Terpenoid-like" Heterocycles.

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.

SUBMITTER: Moore JT

PROVIDER: S-EPMC3614375 | biostudies-literature | 2013 Jan

REPOSITORIES: biostudies-literature

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Catalytic Alkene Cyclization Reactions for the Stereoselective Synthesis of Complex "Terpenoid-like" Heterocycles.

Moore Jared T JT Soldi Cristian C Fettinger James C JC Shaw Jared T JT

Chemical science 20121025 1

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)<sub>3</sub> serves as an effective and practical pre-catalyst. The scope of this reaction is demonstrated with 21 monocyclizations and 14 bicyclization reactions. ...[more]

PMID: 23565327

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