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Synlett 1990; 1990(4): 191-194
DOI: 10.1055/s-1990-21029
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Diastereoselectivity in Center-Face Interaction of Reactants. Synthesis of Tetronic Acid Derivatives from ß-C-Lithiated Acrylates and Aldehydes and Methylation of 5-Deprotonated 4-Amino-2(5H)-furanones1

Harald Jatzke* , Ute Evertz, Richard R. Schmidt
  • *Fakultät Chemie, Universität Konstanz, D-7750 Konstanz, Federal Republic of Germany
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Publikationsdatum:
08. März 2002 (online)

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Center-face interaction of ß-C-lithiated acrylates 2A-12A (the center) with acetaldehyde and benzaldehyde (the face) as reactants afforded tetronic acid esters 2a-12a and 2b, 3b, 5b-12b (4-alkoxy-2(5H)-furanones), respectively, with varying diastereoselectivity. 2(5H)-Furanones t-14A and t-15A, substituted in the 4-position with a chiral pyrrolidino group, react with methyl iodide with very high diastereoselectivity to form the corresponding 5-methyl-2(5H)-furanones t-5a and t-6a. The different types of center-face interactions and their relevance to facial differentiation are discussed.