1234691-45-2Relevant academic research and scientific papers
A new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones via palladium-catalyzed coupling of thioesters
Fuwa, Haruhiko,Mizunuma, Kana,Matsukida, Seiji,Sasaki, Makoto
scheme or table, p. 4995 - 5010 (2011/08/06)
In this paper, we describe a new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones. By exploiting palladium-catalyzed coupling of thioesters with terminal alkynes or alkenylboronic acids, a variety of β-hydroxy ynones or enones, respectively, could be prepared in an efficient manner under mild conditions. AgOTf-promoted intramolecular oxa-conjugate cyclization of β-hydroxy ynones provided 2,6-substituted dihydropyrones in excellent yields. On the other hand, acid-catalyzed cyclization of β-hydroxy enones caused racemization of the product 2,6-substituted tetrahydropyrones due to its reversible nature. Eventually, stereoselective hydrogenation of substituted dihydropyrones was found to be a solid and efficient approach for the synthesis of 2,6-cis-substituted tetrahydropyrone derivatives.
An efficient synthesis of 2,6-disubstituted 2,3-dihydro-4 h -pyran-4-ones via sonogashira coupling of p -toluenethiol esters
Fuwa, Haruhiko,Matsukida, Seiji,Sasaki, Makoto
scheme or table, p. 1239 - 1242 (2010/08/06)
An efficient strategy for the synthesis of 2,6-disubstituted 2,3-dihydro-4H-pyran-4-ones has been developed, which relied on Sonogashira coupling of alkynes and p-toluenethiol esters and AgOTf-promoted 6-endo-dig cyclization of the derived -hydroxy ynones
