Journal
ISRAEL JOURNAL OF CHEMISTRY
Volume 56, Issue 6-7, Pages 499-511Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ijch.201500099
Keywords
cycloisomerization; heterocycles; homo-Nazarov cyclization; molecular diversity; strained rings
Categories
Funding
- National Science Foundation [CHE-1056687]
- NOBCChE
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Since the formal characterization of diversity-oriented synthesis (DOS), identification of effective examples of DOS remains an important endeavor for synthetic and pharmaceutical chemists requiring new strategies to generate broader skeletal diversity. Over the last decade, the formal homo-Nazarov cyclization has been an increasingly popular strategy for the concise assembly of functionalized six-membered rings due to the advent of catalytic methods to promote the transformation under milder reaction conditions. Moreover, using the formal homo-Nazarov cyclization as a mechanistic template, reactions can be strategically devised as an effort towards diversity-oriented synthesis. The resulting homo-Nazarov-inspired reactions are then demonstrated as a means to access broad structural diversity. This review discusses the development of these catalytic approaches and the successful implementation of the formal homo-Nazarov reaction as a viable template for diversity-oriented synthesis.
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