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A Straightforward Route to Homoallyl‐Homocrotylamines Promoted by a Titanium Complex
Author(s) -
Toulot Stéphanie,
Bonnin Quentin,
Comte Virginie,
Adriaenssens Louis,
Richard Philippe,
Le Gendre Pierre
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201262
Subject(s) - chemistry , cationic polymerization , benzotriazole , selectivity , cascade , titanium , sequence (biology) , combinatorial chemistry , stereochemistry , medicinal chemistry , computational chemistry , organic chemistry , catalysis , biochemistry , chromatography
π‐Allyltitanium complexes, generated in situ from 1,3‐dienes and [Cp 2 TiH], 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.