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Unexpected Participation of an Unconjugated Olefin during Nazarov Cyclization of Bridged Bicyclic Dienones
Author(s) -
Giese Sören,
Mazzola Robert D.,
Amann Clare M.,
Arif Atta M.,
West F. G.
Publication year - 2005
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.200501737
Subject(s) - bicyclic molecule , ring (chemistry) , alkene , chemistry , substrate (aquarium) , olefin fiber , stereochemistry , catalysis , medicinal chemistry , organic chemistry , oceanography , geology
Surprising rearrangements in a rigid system : A cyclopropyl ring is formed unexpectedly when a trienone substrate is subjected to the Nazarov cyclization (see scheme). The participation of the unconjugated alkene unit present in the substrate might be a consequence of the complete torquoselectivity of the initial electrocyclic closure. A subsequent rearrangement by a homo‐1,5‐hydrogen shift occurs cleanly to give the final product.