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 - enantioselectivity
