Annulation of Aromatic Imines via Directed C−H Bond Activation

A directed C−H bond activation approach to the synthesis of indans, tetralins, dihydrofurans, dihydroindoles, and other polycyclic aromatic compounds is presented. Cyclization of aromatic ketimines and aldimines containing alkenyl groups tethered at the meta position relative to the imine directing...

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Bibliographic Details
Published in:Journal of organic chemistry 2005-08, Vol.70 (17), p.6775-6781
Main Authors: Thalji, Reema K, Ahrendt, Kateri A, Bergman, Robert G, Ellman, Jonathan A
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Carbon - chemistry
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms
Hydrogen - chemistry
Imines - chemistry
Mescaline - analogs & derivatives
Mescaline - chemical synthesis
Organic chemistry
Preparations and properties
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Summary:A directed C−H bond activation approach to the synthesis of indans, tetralins, dihydrofurans, dihydroindoles, and other polycyclic aromatic compounds is presented. Cyclization of aromatic ketimines and aldimines containing alkenyl groups tethered at the meta position relative to the imine directing group has been achieved using (PPh3)3RhCl (Wilkinson's catalyst). The cyclization of a range of aromatic ketimines and aldimines provides bi- and tricyclic ring systems with good regioselectivity. Different ring sizes and substitution patterns can be accessed through the coupling of monosubstituted, 1,1- or 1,2-disubstituted, and trisubstituted alkenes bearing both electron-rich and electron-deficient functionality.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo050757e