Stereoselective 1, 3-dipolar cycloadditions of nitrones derived from amino acids. Asymmetric synthesis of N-(alkoxycarbonylmethyl)-3-hydroxypyrrolidin-2-ones

…, T Tejero, R Hurtado-Guerrero, R Matute, U Chiacchio…

Index: Merino, Pedro; Greco, Graziella; Tejero, Tomas; Hurtado-Guerrero, Ramon; Matute, Rosa; Chiacchio, Ugo; Corsaro, Antonino; Pistara, Venerando; Romeo, Roberto Tetrahedron, 2013 , vol. 69, # 45 p. 9381 - 9390

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Citation Number: 2

Abstract

Abstract Diastereoselective asymmetric 1, 3-dipolar cycloadditions of N- (alkoxycarbonylmethyl) nitrones derived from glycine, alanine and phenylalanine have been studied both experimentally and theoretically. Asymmetric induction is evaluated by either introducing a chiral group at the nitrone nitrogen atom or by using Oppolzer's sultam acrylamide. In both cases the sense of the asymmetric induction is the same, the (3R, 5R)- ...