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Ring‐Rearrangement Metathesis of 7‐Azanorbornenes as an Entry to 1‐Azabicyclo[ n .3.0]alkenones
Author(s) -
Rojas Víctor,
Carreras Javier,
Avenoza Alberto,
Busto Jesús H.,
Peregrina Jesús M.
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.201300126
Subject(s) - azepine , chemistry , metathesis , ring closing metathesis , stereochemistry , salt metathesis reaction , ring (chemistry) , pyrrolizidine , indolizidine , cope rearrangement , olefin metathesis , organic chemistry , alkaloid , polymerization , polymer
Pyrrolizidine, indolizidine, and pyrrolo[1,2‐ a ]azepine substructures are present in a large number of naturally occurring azabicyclic compounds, which are currently of special interest because of their biological activities. To obtain this class of compounds, we envisioned a ring‐rearrangement metathesis (RRM) process of 7‐azanorbornene systems that incorporates several exocyclic olefin patterns at the nitrogen position. By using this methodology, we have synthesized a set of new 1‐azabicyclo[ n .3.0]alkenones, which include derivatives of pyrrolam. In all cases, only one regioisomer was obtained. Moreover, new spiro compounds with tricyclic structures have been synthesized by using a domino metathesis process that involves a ring‐opening/ring‐closing/ring‐closing metathesis (ROM/RCM/RCM) sequence.