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Catalytic Cyclization of o ‐Alkynyl Phenethylamines via Osmacyclopropene Intermediates: Direct Access to Dopaminergic 3‐Benzazepines
Author(s) -
ÁlvarezPérez Andrea,
GonzálezRodríguez Carlos,
GarcíaYebra Cristina,
Varela Jesús A.,
Oñate Enrique,
Esteruelas Miguel A.,
Saá Carlos
Publication year - 2015
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201505782
Subject(s) - benzazepines , phenethylamines , dopaminergic , chemistry , catalysis , osmium , combinatorial chemistry , apomorphine , stereochemistry , organic chemistry , neuroscience , dopamine , psychology , ruthenium
A novel osmium‐catalyzed cyclization of o ‐alkynyl phenethylamines to give 3‐benzazepines is reported. The procedure allows the straightforward preparation of a broad range of dopaminergic 3‐benzazepine derivatives. Mechanistic investigations revealed that the process takes place via osmacyclopropene intermediates, which were isolated and characterized by X‐ray crystallography.