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Synthesis 2022; 54(03): 589-599
DOI: 10.1055/s-0041-1737125
DOI: 10.1055/s-0041-1737125
short review
Recent Advances on Piancatelli Reactions and Related Cascade Processes
We greatly acknowledge funding from the National Natural Science Foundation of China (Grant Nos. 21801030) and the Fundamental Research Funds for the Central Universities (2021CDJQY-012).
Abstract
The Piancatelli reaction, which is the rearrangement of 2-furylcarbinol to cyclopentenone, involves a key furanoxonium ion intermediate and a furan ring opening-4π electrocyclization process. In recent years, the original oxa-Piancatelli reaction has been extended to a large family of aza- and carbo-Piancatelli reactions and related cascade processes, providing a powerful platform for the construction of diverse functionalized cyclopentenones and polycyclic cyclopentanones. Meanwhile, chiral Brønsted/Lewis acid based catalytic asymmetric approaches to Piancatelli reactions have also been achieved for the assembly of highly valued chiral cyclopentenone scaffolds. In this short review, we present an overview of the recent developments in these areas and focus primarily on reports published in the last five years.
1 Introduction
2 Diastereoselective Oxa-, Aza- and Carbo-Piancatelli Reactions
3 Diastereoselective Cascade Piancatelli Reactions
4 Asymmetric Piancatelli Reactions and Related Cascade Processes
5 Miscellaneous Furanoxonium Ion-Based Rearrangements
6 Conclusion
Key words
Piancatelli reaction - furanoxonium ion - rearrangement - catalysis - functionalized cyclopentenone - diastereoselectivity - enantioselectivityPublication History
Received: 15 September 2021
Accepted after revision: 27 September 2021
Article published online:
15 November 2021
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