Tetrahedron

Stereochemical study of 1, 3-N, X-heterocycles derived from α-aminoacids and formaldehyde. Structural evidence for the existence of the anomeric effect

…, F Carré, A Fruchier, JP Roque, AA Pavia

Index: Selambarom, Jimmy; Carre, Francis; Fruchier, Alain; Roque, Jean Pierre; Pavia, Andre A Tetrahedron, 2002 , vol. 58, # 22 p. 4439 - 4444

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Citation Number: 19

Abstract

We have shown that condensation of l-cysteine methyl ester (8) and l-threonine methyl ester (11) with formaldehyde provides a convenient and efficient access to novel heterocyclic 2: 3 adducts. Depending on the amino acid, the condensation leads to either the N, N′- methylenebis (thiazolidine)(10, l-cys) or-(oxazolidine)(13, l-thr) derivative or to its bicyclo [4.4. 1] undecane isomer (5, l-ser) as the major product of the reaction. The structure of 10, ...