Synthesis, Table of Contents PAPER © Georg Thieme Verlag Stuttgart · New York One-Pot, Four-Component Synthesis of Polyfunctional Sulfones Xiaogen Huang, Pierre Vogel*Institut de chimie moléculaire et biologique de l’Ecole Polytechnique Fédérale de Lausanne, SwitzerlandFax: +4(21)6939375; e-Mail: pierre.vogel@epfl.ch; Recommend Article Abstract Buy Article All articles of this category Abstract The reaction of (E,E)-1-benzyloxy-2-methylpenta-1,3-diene with trimethylsilyl enol ethers derived from acetone or acetophenone with sulfur dioxide precomplexed with ytterbium triflate or (CF3SO2)2NH generates sulfinate intermediates that can be quenched by a variety of electrophiles to afford the corresponding polyfunctional sulfones in one-pot operations. Key words allylation - electron-rich dienes - enoxysilanes - oxyallylation - palladium - sulfinates - sulfones Full Text References References 1 Deguin B. Roulet J.-M. Vogel P. Tetrahedron Lett. 1997, 38: 6197 2 Megevand S. Moore J. Schenk K. Vogel P. Tetrahedron Lett. 2001, 42 : 673 3 Roulet J.-M. Puhr G. Vogel P. Tetrahedron Lett. 1997, 38: 6201 4 Narkevitch V. Schenk K. Vogel P. Angew. Chem., Int. Ed. 2000, 39: 1806 5a Deguin B. Vogel P. J. Am. Chem. Soc. 1992, 114: 9210 5b Fernández T. Sordo JA. Monnat F. Deguin B. Vogel P. J. Am. Chem. Soc. 1998, 120: 13276 5c Roversi E. Monnat F. Schenk K. Vogel P. Braña P. Sordo JA. Chem.-Eur. J. 2000, 6: 1858 6 For hetero-Diels-Alder addition of SeO2, see: Mock WL. McCausland JH. Tetrahedron Lett. 1968, 391 For the hetero-Diels-Alder additions of N-sulfenylamines, see: 7a Wichterle O. Rocek J. Collect. Czech. Chem. Commun. 1954, 19: 282 ; Chem. Abstr. 1955, 49, 1053 7b Mock WL. Nugent RJ. J. Am. Chem. Soc. 1975, 97: 6521 7c Mock WL. Nugent RJ. J. Am. Chem. Soc. 1975, 97: 6526 7d Dittmer DC. Hoey MD. The Chemistry of Sulphinic Acids, Esters and Their Derivations Patai S. Wiley; Chichester: 1990. p.239 7e Bell SI. Parvez M. Weinreb SM. J. Org. Chem. 1991, 56: 373 For the hetero-Diels-Alder additions of sulfines, see: 8a Zwanenburg B. Thijs L. Broens JB. Strating J. Recl. Trav. Chim. Pays-Bas 1972, 91: 443 8b Porskamp PATW. der Liij MV. Lammerink BHM. Zwannenburg B. Recl. Trav. Chim. Pays-Bas 1983, 102: 100 8c Porskamp PATW. Haltiwanger RC. Zwanenburg B. Tetrahedron Lett. 1983, 24: 2035 9 For the hetero-Diels-Alder additions of SO2 to bis(imides), see: Natsugari H. Whittle RR. Weinreb SM. J. Am. Chem. Soc. 1984, 106: 7867 ; and references cited therein For the reaction of S2 to 1,3-dienes, see: 10a Steliou K. Gareau Y. Milot G. Salama P. J. Am. Chem. Soc. 1990, 112: 7819 10b Gilchrist TL. Wood JE. J. Chem. Soc., Perkin Trans.1 1992, 9 For the first examples of hetero-Diels-Alder additions of SO2, see: 11a Heldeweg RF. Hogeveen H. J. Am. Chem. Soc. 1976, 98: 2341 11b Durst T. Tétreault-Ryan L. Tetrahedron Lett. 1978, 2353 12 For the observation of the first crystalline sultine, see: Roversi E. Scopelliti R. Solari E. Estoppey R. Vogel P. Braña P. Menéndez B. Sordo JA. Chem. Commun. 2001, 1214 To our knowledge, one-pot four-component synthesis of sulfones had never been described thus far. For other methods of open-chain sulfone synthesis, see: 13a Schank K. The Chemistry of Sulphones and Sulfoxides Patai S. Rappoport Z. Stirling CJM. Wiley; Chichester: 1988. p.165-231 13b Schank K. In Syntheses of Sulphones, Sulphoxides and Cyclic Sulphides Patai S. Rappoport Z. Wiley; Chichester: 1994. p.1-67 13c Schank K. Schott N. In Syntheses of Sulphones, Sulphoxides and Cyclic Sulphides Patai S. Rappoport Z. Wiley; Chichester: 1994. p.69-108 14 For examples of multicomponent syntheses, see Ref.13 of preceding report: Bouchez, L.; Vogel, P. Synthesis, preceding paper. 15a Grover JR. Walters EA. Newman JK. White MG. J. Am. Chem. Soc. 1990, 112: 6499 15b Xu L.-W. Taleb-Benbiab A. Nemes L. Kuczkowski RL. J. Am. Chem. Soc. 1993, 115: 5723 16 For related methylsulfones derived from other dienes than 9 and other enoxysilanes than 10 and 11, see: Narkevitch V. Megevand S. Schenk K. Vogel P. J. Org. Chem. 2001, 66: 5080 17 Tsuji J. Palladium Reagents and Catalysts, Innovations in Organic Synthesis Wiley; Chichester: 1995. p.351-353 18a Tsuji J. Minami I. Acc. Chem. Res. 1987, 20: 140 18b Tsuji J. Tetrahedron 1986, 42: 4361 For example of bioactive polyfunctional sulfones, see: 19a Freskos JN. Mischke BV. DeCrescenzo GA. Heintz R. Getman DP. Howard SC. Kishore NN. McDonald JJ. Murie GE. Rangwala S. Swearingen CA. Voliva C. Welsch DJ. Bioorg. Med. Chem. Lett. 1999, 9: 943 19b Jones PB. Parrish NM. Houston TA. Stapon A. Bansal NP. Dick JD. Townsend CA. J. Med. Chem. 2000, 43: 3304