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Pure Appl. Chem., 1996, Vol. 68, No. 4, pp. 925-930

http://dx.doi.org/10.1351/pac199668040925

The sulfinyl group as a chiral inductor in asymmetric Diels-Alder reactions

J. L. G. Ruano, J. C. Carretero, M. C. Carreno, L. M. M. Cabrejas and A. Urbano

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  • Khiar Noureddine, Salvador Álvaro, Chelouan Ahmed, Alcudia Ana, Fernández Inmaculada: “Sulfolefin”: Highly modular mixed S/Olefin ligands for enantioselective Rh-catalyzed 1,4-addition. Biomol Chem 2012, 10, 2366. <http://dx.doi.org/10.1039/c2ob07132k>
  • Okamura Hiroaki, Urabe Fumiya, Hamada Toshiyuki, Iwagawa Tetsuo: Base-Catalyzed Asymmetric Diels^|^ndash;Alder Reaction of 3-Hydroxy-2-pyrone and Simple Aryl Vinyl Sulfoxide: Asymmetric Synthesis of Carbaketopyranoses. Bull. Chem. Soc. Jpn. 2012, 85, 631. <http://dx.doi.org/10.1246/bcsj.20110257>
  • Okamura Hiroaki, Iwagawa Tetsuo, Hamada Toshiyuki: Development of Catalytic Diels-Alder Reactions Based on Diene Activation Methodology, and Their Synthetic Applications for Biologically Active Cyclohexeneoxides and Carbasugars. J Syn Org Chem Jpn 2012, 70, 227. <http://dx.doi.org/10.5059/yukigoseikyokaishi.70.227>
  • Latorre Alfonso, Urbano Antonio, Carmen Carreño M.: Synthesis and chiroptical properties of ferrocene-[4]-helicenequinones: kinetic resolution of a planar-chiral diene. Chemical Communication 2011, 47, 8103. <http://dx.doi.org/10.1039/c1cc12921j>
  • GARCIA RUANO J. L., CARRETERO J. C., CARRENO M. C., MARTIN CABREJAS L. M., URBANO A.: ChemInform Abstract: The Sulfinyl Group as a Chiral Inductor in Asymmetric Diels-Alder Reactions. ChemInform 2010, 27, no. <http://dx.doi.org/10.1002/chin.199650276>
  • Pellissier Hélène: Use of chiral sulfoxides in asymmetric synthesis. Tetrahedron 2006, 62, 5559. <http://dx.doi.org/10.1016/j.tet.2006.03.093>
  • Pezzotti Fabio, Okrasa Krzysztof, Therisod Michel: Bienzymatic synthesis of chiral heteroaryl-methyl-sulfoxides. Tet Asymm 2005, 16, 2681. <http://dx.doi.org/10.1016/j.tetasy.2005.07.004>
  • García Ruano José L., Gamboa Antonio Esteban, Gutiérrez Lorena González, Martín Castro Ana M., Rodríguez Ramos Jesús H., Yuste Francisco: Synthesis and Diels−Alder Reactions of a New Kind of Chiral Dienophiles:  Cyclic Vinyl-p-tolylsulfilimines. Org Lett 2000, 2, 733. <http://dx.doi.org/10.1021/ol991224t>
  • Rumbo Antonio, Castedo Luis, Mascareñas JoséL.: Use of a sulfinyl tether to control diastereofacial selectivity in [5C + 2C] pyrone-alkene cycloadditions. Tetrahetron Lett 1997, 38, 5885. <http://dx.doi.org/10.1016/S0040-4039(97)01310-5>
  • Aversa Maria C., Barattucci Anna, Bonaccorsi Paola, Giannetto Placido: Chiral sulfinyl-1,3-dienes. Synthesis and use in asymmetric reactions. Tet Asymm 1997, 8, 1339. <http://dx.doi.org/10.1016/S0957-4166(97)00158-4>
  • Carretero Juan C, García Ruano JoséL, Martín Cabrejas Luisa M: Asymmetric Diels-Alder reaction of (S)-α-p-tolylsulfinyl α,β-unsaturated esters: the role of the sulfinyl group in asymmetric Diels-Alder reactions of vinylsulfoxides. Tet Asymm 1997, 8, 2215. <http://dx.doi.org/10.1016/S0957-4166(97)00231-0>