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Synfacts 2008(8): 0878-0878
DOI: 10.1055/s-2008-1078543
DOI: 10.1055/s-2008-1078543
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Chiral Phosphine-Catalyzed Synthesis of γ-Butenolides
Y.-Q. Jiang, Y.-L. Shi, M. Shi*
Shanghai Institute of Organic Chemistry, P. R. of China
Further Information
Publication History
Publication Date:
23 July 2008 (online)
Significance
The authors report an efficient phosphine 1 catalyzed transformation of Morita-Baylis-Hillman (MBH) acetates 2 and furan 3 to γ-butenolides 4. The reaction pathway is assumed to occur via an enone intermediate formation of 1 with MBH acetate 2. This adduct presumably undergoes Diels-Alder addition with furan 4. The effect of water as an additive is discussed to be beneficial for the subsequent Grob-type fragmentation of the sterically fixed endo-Diels-Alder adduct, liberating the product and the catalyst.