ChemInform Abstract: Catalytic Alkene Cyclization Reactions for the Stereoselective Synthesis of Complex 'Terpenoid-Like' Heterocycles
- Resource Type
- Authors
- James C. Fettinger; Jared T. Moore; Cristian Soldi; Jared T. Shaw
- Source
- ChemInform. 44
- Subject
- chemistry.chemical_classification
chemistry
Alkene
Single step
Stereoselectivity
General Medicine
Combinatorial chemistry
Terpenoid
Catalysis
Stereocenter
- Language
- ISSN
- 0931-7597
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.