2002 diastereoselective syntheses, enantioselective syntheses

diastereoselective syntheses, enantioselective syntheses (incl. cis/trans-isomerism)O 0031

51 - 033Cyclic Vinyl p-Tolyl Sulfilimines as Chiral Dienophiles: Diels–AlderReactions with Furan and Acyclic Dienes. — Complete π-facialselectivity is observed for all reactions of sulfimine (I) with dienes (II), (IV),and (VIII). An almost complete exo-selectivity is found for the reaction withfuran, whereas with acyclic dienes, almost complete endo-selectivity occurs. Thestereo- and regiochemical behavior of sulfimine (I) is compared with that of itsprecursor (Z)-p-tolylsulfinylacrylonitrile. It is found that both dienophiles canbe considered as complementary from stereo- and regiochemical points of view.— (GARCIA RUANO, JOSE L.; ALEMPARTE, CARLOS; CLEMENTE,FERNANDO R.; GONZALEZ GUTIERREZ, LORENA; GORDILLO, RUTH;MARTIN CASTRO, ANA M.; RODRIGUEZ RAMOS, JESUS H.; J. Org.Chem. 67 (2002) 9, 2919-2925; Dep. Quim. Org., Univ. Auton., Cantoblanco,E-28049 Madrid, Spain; EN)

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