[3,3]-sigmatropic rearrangement/5-exo-dig cyclization reactions of benzyl alkynyl ethers: Synthesis of substituted 2-indanones and indenes
Substituted benzyl alkynyl ethers, prepared from the corresponding α-alkoxy ketones in a two-step sequence involving enol triflate formation and KOtBu-induced E2 elimination, undergo [3,3]-sigmatropic rearrangement/ intramolecular 5-exo-dig cyclization at 60 °C to form substituted 2-indanones in good overall yields. 1,3-cis-Disubstituted-2-indanones are formed preferentially when the benzylic substituent R1 is bulky. Substituted indenes may be prepared from 2-indanones in high yields by Horner-Wadsworth-Emmons reaction.
Tudjarian, Armen A.,Minehan, Thomas G.
p. 3576 - 3581
(2011/06/25)
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