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Synlett 2000; 2000(5): 0611-0614
DOI: 10.1055/s-2000-6597
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A New, General Approach to Substituted 3-Diethoxyphosphoryl-2,5-dihydro-2-furanones

Tomasz Janecki* , Andrzej Kuś, Henryk Krawczyk, Edyta Błaszczyk
  • *Institute of Organic Chemistry, Technical University, Żeromskiego 116, 90-924 Łódź, Poland; Fax (48-42)636-55-30; E-mail: tjanecki@ck-sg.p.lodz.pl
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Publication Date:
31 December 2000 (online)

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Two synthetic methods leading to mono- or di-substituted 3-diethoxyphosphoryl-2,5-dihydro-2-furanones 8a - g are presented. Allylic bromination of the 2-diethoxyphosphoryl-2-alkenoates 6a - d and subsequent lactonization of the bromides 7a - d constitute the first method. The second method involves syn-hydroxylation of the 2-diethoxyphosphoryl-3-alkenoic acids 9a - c, e - g followed by lactonization and elimination of water from diols 10a - c, e - g. Syntheses of the starting 6a - d and 9a - c, g - e are also described.

Knoevenagel condensation - dihydroxylations - cyclizations - phosphorylated lactones - 2,5-dihydro-2-furanones