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Butenolide Synthesis from Functionalized Cyclopropenones

Sean S. Nguyen, Andrew J. Ferreira, Zane G. Long, Tyler K. Heiss, Robert S. Dorn, R. David Row and Jennifer A. Prescher*

*Departments of Chemistry, Molecular Biology & Biochemistry, Pharmaceutical Sciences, University of California, Irvine, California 92697, United States, Email:

S. S. Nguyen, A. J. Ferreira, Z. G. Long, T. K. Heiss, R. S. Dorn, R. D. Row, J. A. Prescher, Org. Lett., 2019, 21, 8673-8678.

DOI: 10.1021/acs.orglett.9b03298

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Cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. A subsequent cyclization with a pendant hydroxy group provides butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and tolerates a broad range of functional groups.

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Key Words

butenolides, organocatalysis

ID: J54-Y2019