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Ready Access to Alkylidenecyclopentenones by Nazarov Cyclization/β‐Elimination of 2‐Hydroxyalkyl‐1,4‐dien‐3‐ones
Author(s) -
Scadeng Owen,
West F. G.
Publication year - 2014
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.201301537
Subject(s) - chemistry , deprotonation , regioselectivity , substituent , yield (engineering) , olefin fiber , conjugated system , medicinal chemistry , stereochemistry , organic chemistry , catalysis , ion , materials science , polymer , metallurgy
Cross‐conjugated dienones bearing α‐hydroxyalkyl substituents readily undergo Nazarov cyclization followed by deprotonation of the resulting cyclopentenyl cation, and β‐elimination of the exocyclic hydroxy group to form alkylidenecyclopentenones in moderate yield. The deprotonation step occurs with complete regioselectivity opposite to the hydroxyalkyl substituent, with preferential introduction of an endocyclic olefin. The transformation is tolerant of a variety of substituents and occurs under relatively mild conditions.