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RESEARCH PRODUCT

A Straightforward Route to Homoallyl-Homocrotylamines Promoted by a Titanium Complex

Philippe RichardVirginie ComteLouis AdriaenssensStephanie ToulotQuentin BonninPierre Le Gendre

subject

chemistry.chemical_compoundBenzotriazoleCascade reactionChemistryOrganic ChemistryCationic polymerizationOrganic chemistryPhysical and Theoretical ChemistrySigmatropic reactionSelectivityCombinatorial chemistryA titanium

description

I�-Allyltitanium complexes, generated in situ from 1,3-dienes and Cp2TiH, react with benzotriazole derivatives to give homoallylic amines in good yields. Under similar conditions, triple cascade reactions (allyltitanation followed by cationic 2-aza-Cope rearrangement followed by a second allyltitanation) occur from bis(benzotriazolyl) compounds affording a straightforward route to homoallyl-(E)-homocrotylamines. A theoretical study provides further insight into the factors that govern the selectivity of this sequence of reactions. The titanium-promoted reductive coupling of 1,3-dienes with bis(benzotriazolyl) compounds as substrates led selectively to homoallyl-homocrotylamines through a triple cascade reaction (allyltitanation - cationic 2-aza-Cope rearrangement - allyltitanation). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

yearjournalcountryeditionlanguage
2012-12-14European Journal of Organic Chemistry
https://doi.org/10.1002/ejoc.201201262