ChemInform Abstract: Synthesis and Asymmetric Diels-Alder Reactions of Enantiopure 3-( Alkylsulfinyl)-1-methoxy-1,3-butadienes.

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  • 1997 sulfoxides, sulfones, sulfenes and derivatives

    sulfoxides, sulfones, sulfenes and derivatives (acyclic compounds)P 0450

    48 - 090Synthesis and Asymmetric Diels-Alder Reactions of Enantiopure 3-(Alkylsulfinyl)-1-methoxy-1,3-butadienes. Sulfinyl dienes, whichare prepared by addition of sulfenic acids to the alkynes (II) with varyingdiastereoselectivity, undergo regioselective Diels-Alder reactions with methylacrylate. The uncatalyzed reaction proceeds with low stereocontrol, whereasin the presence of LiClO4 or ZnCl2 high stereoselectivity is observed. (AVERSA, M. C.; BARATUCCI, A.; BONACCORSI, P.; GIANNETTO, P.;JONES, D. N.; J. Org. Chem. 62 (1997) 13, 4376-4384; Dip. Chim. Org. Biol.,Univ. Messina, I-98166 Messina, Italy; EN)

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