Synthesis
DOI: 10.1055/a-1519-1670
review

Synthesis and Applications of Cyclopropanones and their Equivalents as Three-Carbon Building Blocks in Organic Synthesis

Yujin Jang
1  Chemistry, North Carolina State University, Raleigh, United States (Ringgold ID: RIN6798)
,
1  Chemistry, North Carolina State University, Raleigh, United States (Ringgold ID: RIN6798)
,
2  Chemistry, North Carolina State University, Raleigh, United States (Ringgold ID: RIN6798)
› Author Affiliations

Cyclopropanone derivatives constitute highly strained cycloalkanones with promising applications as three-carbon building blocks in organic synthesis. Due to the presence of a ketone in such a small ring system, all C–C bonds and the carbonyl group are considered to be labile in suitable conditions, leading to a wide variety of synthetic disconnections, including nucleophilic addition, ring expansion, ring-opening and (formal) cycloaddition. Despite their synthetic potential, the widespread adoption of cyclopropanones as substrates has been considerably hampered by the difficulties associated with the preparation and storage of such unstable compounds, prompting the development of cyclopropanone surrogates that can equilibrate to parent ketone in situ via elimination. This review summarizes the syntheses and applications of cyclopropanone derivatives and their equivalents, and offers a perspective of the state of the field as well as its expected future directions.



Publication History

Received: 08 May 2021

Accepted after revision: 27 May 2021

Publication Date:
27 May 2021 (online)

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