Regio- and Stereoselective Addition of Allylmetal Reagents to Pyridinium−π and Quinolinium−π Complexes
Authors:
- 16 March 2007
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 9 (8) , 1477-1480
Abstract
[reaction: see text] Regio- and stereoselective allylation of pyridinium and quinolinium salts was performed by the addition of allylindium and allyltributyltin reagents toward intermediary cation-pi complexes. The reaction with allylindium and allyltributyltin reagents afforded a 1,2-adduct, whereas the addition of a prenylindium reagent gave a 1,4-adduct with good regio- and stereoselectivities. X-ray structural analysis, 1H NMR studies, and DFT calculations elucidated the intermediary cation-pi complex formation with face-to-face orientation.Keywords
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