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Butenolide Synthesis from Functionalized Cyclopropenones.

ABSTRACT: 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 ?- and ?-substituted butenolides.

SUBMITTER: Nguyen SS

PROVIDER: S-EPMC7456522 | biostudies-literature | 2019 Nov

REPOSITORIES: biostudies-literature

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Butenolide Synthesis from Functionalized Cyclopropenones.

Nguyen Sean S SS Ferreira Andrew J AJ Long Zane G ZG Heiss Tyler K TK Dorn Robert S RS Row R David RD Prescher Jennifer A JA

Organic letters 20191017 21

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, y ...[more]

PMID: 31622107

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