An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers
An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.
Gaykar, Rahul N.,George, Malini,Guin, Avishek,Bhattacharjee, Subrata,Biju, Akkattu T.
p. 3447 - 3452
(2021/05/04)
Thioaldehyde Diels-Alder Reactions
Thioaldehydes containing virtually any α-substitutent can be generated by photofragmentation of phenacyl sulfides.Donor-substituted derivatives are reactive toward electron-rich dienes and give 2 + 4 cycloadducts with regiochemistry corresponding to advan
Vedejs, E.,Eberlein, T. H.,Mazur, D. J.,McClure, C. K.,Perry, D. A.,et al.
p. 1556 - 1562
(2007/10/02)
Dienophilic Thioaldehydes
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Vedejs, E.,Eberlein, T. H.,Varie, D. L.
p. 1445 - 1447
(2007/10/02)
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