Open AccessButenolide Synthesis from Functionalized Cyclopropenones
Author(s) -
Sean S Nguyen,
Andrew J. Ferreira,
Zane G Long,
Tyler K. Heiss,
Robert S Dorn,
R. David Row,
Jennifer A. Prescher
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b03298
Subject(s) - butenolide , ketene , chemistry , catalysis , combinatorial chemistry , phosphine , ring (chemistry) , functional group , organic chemistry , polymer
A general method to synthesize substituted butenolides from hydroxymethylcyclopropenones is reported. Functionalized cyclopropenones undergo ring-opening reactions with catalytic amounts of phosphine, forming reactive ketene ylides. These intermediates can be trapped by pendant hydroxy groups to afford target butenolide scaffolds. The reaction proceeds efficiently in diverse solvents and with low catalyst loadings. Importantly, the cyclization is tolerant of a broad range of functional groups, yielding a variety of α- and γ-substituted butenolides.