AI Article Synopsis
- A new method has been created for producing five-membered heterocyclic compounds using hydroxylated enynes, utilizing small amounts of a specific acid catalyst (F(3)CSO(3)H).
- This process leads to the generation of unique compounds with an allene group positioned at the third carbon, especially when certain groups (R(1), R(2)) are present.
- The reaction takes place through a domino mechanism involving an allene carbocation intermediate, which can react with olefins, allowing for the formation of diverse novel chemical structures.
Article Abstract
A mild and direct pathway for the formation of five-membered heterocyclic compounds from hydroxylated enynes has been developed. In this reaction, hydroxylated enynes were selectively transformed into five-membered heterocyclic compounds 2, with an allene moiety at the 3-position, in the presence of F(3) CSO(3) H (0.1 mol %). When R(1) , R(2) =Ph, diphenylvinyl-2,3-dihydro-1H-pyrrole (2 y) was obtained. With HSbF(6) (5 mol %) as the catalyst, polycyclic skeletons 3 and 4 with adjacent stereocenters were obtained. When R(1) =H and R(2) =styrene, 1,3-dienyl-2,5-dihydro-1H-pyrrole (6 as) was formed. This Brønsted acid catalyzed domino process involves the formation of an allene carbocation intermediate, which can be readily trapped by olefins to give various novel five-membered heterocyclic skeletons.
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| http://dx.doi.org/10.1002/chem.201002222 | DOI Listing |
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