A straightforward route to homoallyl-homocrotylamines promoted by a titanium complex

Toulot, S. and Bonnin, Q. and Comte, V. and Adriaenssens, L. and Richard, P. and Le Gendre, P. (2013) A straightforward route to homoallyl-homocrotylamines promoted by a titanium complex. European Journal of Organic Chemistry, 2013 (4). pp. 736-741. ISSN 1434193X

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Abstract

�-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.

Additional Information:cited By 0 The final published version of this article can be accessed at https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201201262. Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim
Keywords:methadology
Subjects:F Physical Sciences > F100 Chemistry
Divisions:College of Science > School of Chemistry
ID Code:22738
Deposited On:25 Jul 2018 10:31

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