Diastereoselectivity in Center-Face Interaction of Reactants. Synthesis of Tetronic Acid Derivatives from β-C-Lithiated Acrylates and Aldehydes and Methylation of 5-Deprotonated 4-Amino-2(5H)-furanones¹

1 January 1990

journal article
letter
Published by Georg Thieme Verlag KG in Synlett

Vol. 1990 (04) , 191-194
https://doi.org/10.1055/s-1990-21029

Abstract

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.

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Diastereoselectivity in Center-Face Interaction of Reactants. Synthesis of Tetronic Acid Derivatives from β-C-Lithiated Acrylates and Aldehydes and Methylation of 5-Deprotonated 4-Amino-2(5H)-furanones1

Abstract

Keywords

Diastereoselectivity in Center-Face Interaction of Reactants. Synthesis of Tetronic Acid Derivatives from β-C-Lithiated Acrylates and Aldehydes and Methylation of 5-Deprotonated 4-Amino-2(5H)-furanones¹