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

被引：36
作者：
Millemaggi, Alessia [1 ]
Perry, Alexis [1 ]
Whitwood, Adrian C. [1 ]
Taylor, Richard J. K. [1 ]
机构：
[1] Univ York, Dept Chem, York YO10 5DD, N Yorkshire, England
来源：
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2009年 / 2009卷 / 18期
基金：
英国工程与自然科学研究理事会;
关键词：
Horner-Wadsworth-Emmons olefination; Phosphonates; Enolate arylation; Palladium catalysis; Oxindoles; Telescoped reactions; INTRAMOLECULAR ALPHA-ARYLATION; PALLADIUM-CATALYZED SYNTHESIS; POLYSUBSTITUTED INDOLES; H FUNCTIONALIZATION; CARBENE LIGANDS; OXINDOLES; CYCLOADDITION; AMMOSAMIDES; FACILE; ACCESS;
D O I：
10.1002/ejoc.200900294
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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)
引用
收藏
页码：2947 / 2952
页数：6
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