4.5 Review

Overview of 6π 1,5-Electrocyclization over the Past 40 Years

期刊

CHINESE JOURNAL OF CHEMISTRY
卷 41, 期 6, 页码 725-740

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.202200583

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Electrocyclization; Five-membered Rings; Heterocyclic Compounds; Pericyclic Reaction

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This article reviews the development of 1,5-electrocyclizations, including stepwise, stoichiometric, or catalytic approaches. It also discusses 1,5-electrocyclizations involving heteroatoms (N, O, P, S) and provides a summary of related mechanistic studies.
Comprehensive SummaryAs an important part of pericyclic reaction, 6 pi 1,5-electrocyclization plays an important role in organic synthesis and chemical theory. Many types of five-membered rings could be constructed via 1,5-electrocyclization with high atom economy. Some elegant works have been reported in this field in the past few decades. However, it still needs a lot of effort in further advancements of 1,5-electrocyclization. This review summarized the development of 1,5-electrocyclization relying on stepwise, stoichiometric, or catalytic approaches. The 1,5-electrocyclization reaction will be divided into three categories: aza 1,5-electrocyclization, all-carbon 1,5-electrocyclization and other heteroatoms (O, P, S) involved 1,5-electrocyclization, and related mechanistic studies will also be involved in this review.

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