Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 18, Pages 3621-3633Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300134
Keywords
Synthetic methods; Cyclization; Carbocations; Cyclopentanes
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Funding
- National Science Foundation (NSF) [CHE-0847851]
- National Institutes of Health [NIGMS R01 GM079364]
- Direct For Mathematical & Physical Scien [1152725] Funding Source: National Science Foundation
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM079364] Funding Source: NIH RePORTER
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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.
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