New 4-spiroannulated tetrahydroisoquinolines by a one-pot sequential procedure. isolation and characterization of sigma-alkylpalladium heck intermediates.
A simple and efficient entry to new tetrahydroisoquinolines 4-spiroannulated to a five-membered heterocyclic ring has been achieved starting from secondary N-allylamines and involving sequential 2-iodobenzylation/intramolecular Heck reaction/1,3-dipolar cycloaddition. A variety of Heck cyclization conditions were surveyed. When using Pd(PPh(3))(4) as catalyst, stable sigma-alkylpalladium iodide complexes were isolated and characterizated.
Beccalli
Egle M
EM
Istituto di Chimica Organica "A. Marchesini", Facoltà di Farmacia, Università di Milano, via Venezian 21, 20133 Milano, Italy.
Broggini
Gianluigi
G
Martinelli
Michela
M
Masciocchi
Norberto
N
Sottocornola
Silvia
S
D009682:Magnetic Resonance Spectroscopy; D010165:Palladium / Q000737:chemistry*; D044005:Tetrahydroisoquinolines / Q000138:chemical synthesis* / Q000737:chemistry / Q000302:isolation & purification
D044005:Tetrahydroisoquinolines; D010165:Palladium