Unexpected Participation of an Unconjugated Olefin during Nazarov Cyclization of Bridged Bicyclic Dienones | Zendy

Giese Sören | Zendy; Mazzola Robert D. | Zendy; Amann Clare M. | Zendy; Arif Atta M. | Zendy; West F. G. | Zendy

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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.

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