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200517.fm Page 61 Friday, March 18, 2005 2:52 PM
2005
C-C bond formation
O 0282
Efficient Baylis—Hillman Reactions of Cyclic Enones in Methanol as Catalyzed
Methoxide Anion. — It is shown for the first time that Baylis—Hillman reaction
17- 058 by
can be catalyzed efficiently by the methoxide anion. Various cyclic enones and aldehydes react successfully under these conditions, but acrylates and acrylonitrile do not.
The reaction follows an oxa-Michael addition/aldol pathway or proceeds via γ-dienolate anion intermediates. — (LUO, S.; MI, X.; XU, H.; WANG, P. G.; CHENG*, J.-P.;
J. Org. Chem. 69 (2004) 24, 8413-8422; Cent. Mol. Sci., Inst. Chem., Chin. Acad.
Sci., Beijing 100080, Peop. Rep. China; Eng.) — Jannicke
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