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Synthesis of Highly Substituted 2,3-Dihydro-1H-pyrrole Derivatives via a Tandem Regioselective Addition of Nitrones to 1,3-Enynes with Subsequent Rearrangement

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journal contribution
posted on 21.03.2008, 00:00 by Sivaperuman Saravanan, Ismail Abulkalam Azath, Shanmugam Muthusubramanian
A novel method for the synthesis of 1,3-enynes is described through oxidative cyclization of the semicarbazones of Michael adducts having potential nitrile functionality. Reaction of these 1,3-enynes with diaryl nitrones has yielded a diastereomeric mixture of highly substituted 2,3-dihydro-1H-pyrrole derivatives via a tandem regioselective addition with subsequent rearrangement.