(R)-or (S)-4-(3-hydroxy-4, 4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid as a new chiral auxiliary for solid phase asymmetric Diels–Alder reactions

…, F Escale, J Iapichella, M Rolland, J Martinez

Index: Akkari, Rhalid; Calmes, Monique; Escale, Francoise; Iapichella, Julien; Rolland, Marc; Martinez, Jean Tetrahedron Asymmetry, 2004 , vol. 15, # 16 p. 2515 - 2525

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Citation Number: 24

Abstract

The synthesis of enantiopure (R)-and (S)-4-(3-hydroxy-4, 4-dimethyl-2-oxopyrrolidin-1-yl) benzoic acid is described and the corresponding supported chiral acrylate derivative has been used as a dienophile in solid phase asymmetric Diels–Alder reactions with different dienes. In all cases, the reaction gave the expected compound in good yield and with high regio or endo selectivity. Moreover, a high facial diastereoselectivity (86–99% de) was ...