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Telescoped Enolate Arylation/HWE Procedure for the Preparation of 3‐Alkenyl‐Oxindoles: The First Synthesis of Soulieotine
Author(s) -
Millemaggi Alessia,
Perry Alexis,
Whitwood Adrian C.,
Taylor Richard J. K.
Publication year - 2009
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200900294
Subject(s) - chemistry , adduct , palladium , intramolecular force , formaldehyde , microwave irradiation , organic chemistry , sequence (biology) , catalysis , biochemistry
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. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)