Abstract

GARCIA RUANO, Jose Luis  and  ZARZUELO ALBA, María M.. Comportamiento de N-Sulfinil acrilamidas como dienófilos quirales. Rev. Soc. Quím. Méx [online]. 2001, vol.45, n.4, pp.208-213. ISSN 0583-7693.

In order to establish the influence of the N-sulfinyl group on the behavior of the acrylamides as chiral dienophiles, the reaction of (S)-(E)-N-benzyl-N-p-tolylsulfinyl-2-butenamide (2) with cyclopentadiene has been studied under different conditions. A moderate reactivity under high pressures or catalysts, a very high endo/exo selectivity (97:3) and a significant facial diastereoselectivity (de up to 60 %) are their most significant features.

Keywords : N-sulfinyl; acrylamides; Diels Alder; S)-(E)-N-benzyl-N-p-tolylsulfinyl-2-butenamide; cyclopentadiene; estereoselectivity.

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