Conversion of isomeric 2: 3 adducts (aminoacid–formaldehyde) to N-acyl-pseudoprolines derivatives

J Sélambarom, J Smadja, AA Pavia

Index: Selambarom, Jimmy; Smadja, Jacqueline; Pavia, Andre A. Tetrahedron Letters, 2005 , vol. 46, # 4 p. 615 - 617

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Citation Number: 4

Abstract

Reaction of acyl chlorides or acid anhydrides with isomeric 2: 3 adducts derived from condensation of l-serine (), l-threonine () and l-cysteine () methyl esters with formaldehyde afforded N-acyl-pseudoprolines in various yields. These 2: 3 adducts can be considered as synthetic equivalents of oxaproline and thiaproline moieties. The present work revealed the versatile behaviour of the two 2: 3 adducts as a consequence of the ring-chain ...