Journal
ORGANIC LETTERS
Volume 10, Issue 3, Pages 429-432Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol702462w
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- NIGMS NIH HHS [R01 GM071779-02, R01 GM071779, R01GM071779, R01 GM071779-01A1] Funding Source: Medline
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This paper describes the phosphine-catalyzed annulation of methyl allenoate with various aromatic aldehydes to form 6-aryl-4-methoxy-5,6-dihydro-2-pyrones. In this reaction, the addition of an alcohol was necessary to induce dihydropyrone formation, with the optimal agent being methanol. Moreover, the addition of n-butyllithium suppressed the formation of the noncyclized product, leading to the exclusive isolation of the dihydropyrone. This method provides an efficient, one-step route toward disubstituted dihydropyrones from simple, stable starting materials.
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