Telescoped Enolate Arylation/HWE Procedure for the Preparation of 3-Alkenyl-Oxindoles: The First Synthesis of Soulieotine

A telescoped sequence involving palladium-catalysed intramolecular enolate arylation followed by an in situ HWE olefination has been developed to provide rapid access to 3-alkenyl-oxindoles. This one-pot process, which is greatly accelerated by microwave irradiation, proceeds with low loadings of palladium(II) acetate (0.2-1.0 mol-%), and has been used to prepare a range of adducts derived from aromatic, heteroaromatic and aliphatic aldehydes as well as formaldehyde. In addition, further elaboration of the formaldehyde adducts are described. The applicability of the process has been established by carrying out the first synthesis of Soulieotine, a constituent of a traditional Chinese medicine. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)