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Beyond the Divinyl Ketone: Innovations in the Generation and Nazarov Cyclization of Pentadienyl Cation Intermediates
Author(s) -
Spencer III William T.,
Vaidya Tulaza,
Frontier Alison J.
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.201300134
Subject(s) - chemistry , ketone , heteroatom , nucleophile , ring (chemistry) , nucleophilic addition , combinatorial chemistry , organic chemistry , catalysis
The requirement for new strategies for synthesizing five‐membered carbocycles has driven an expansion in study of the Nazarov cyclization. This renewed interest in the reaction has led to the discovery of several interesting new methods for generating the pentadienyl cation intermediates central to the cyclization. Methods reviewed include carbon‐heteroatom ionization, double bond functionalization, nucleophilic addition, or electrocyclic ring opening. Additional variations, such as iso‐ and imino‐Nazarov cyclization, employ unconventional substrates to produce new pentacycles. Here we provide an overview of these unconventional, yet highly useful versions of the Nazarov cyclization.