230
L. Bouchez, P. Vogel
PAPER
(12) -Keto sulfones can be prepared by oxidation of -hydroxy
sulfones arising from the addition of -sulfonyl carbanions
to aldehydes and ketones; e.g. (a) Tavares, D. F.; Vogt, P. F.
Can. J. Chem. 1967, 45, 1519. (b) Julia, M.; Uguen, D.;
Callipolitis, A. Bull. Soc. Chim. Fr. 1976, 519. (c) Capet,
M.; Cuvigny, T.; Du Penhoat, C. H.; Julia, M.; Loomis, G.
Tetrahedron Lett. 1987, 28, 6273. (d) Chemla, F.; Julia, M.;
Uguen, D. Bull. Soc. Chim. Fr. 1994, 131, 639. From the
addition of sulfinates to epoxides, see, for example:
(e) Still, I. W. J.; Ablenas, F. J. Synth. Commun. 1982, 12,
1103. (f) Biswas, G. K.; Bhattacharyya, P. Synth. Commun.
1991, 21, 569.
(13) For other examples of multicomponent synthesis methods,
see, for example: (a) Ugi, I.; Steinbrucker, C. Chem. Ber.
1961, 94, 734. (b) Fetzer, U.; Ugi, I. Liebigs Ann. Chem.
1962, 659, 184. (c) Ugi, I.; Offermann, K.; Herlinger, H.;
Marquarding, D. Liebigs Ann. Chem. 1967, 709, 1.
(d) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J.
Chem. Soc., Chem. Commun. 1971, 1. (e) Obrecht, R.;
Toure, S.; Ugi, I. Heterocycles 1984, 21, 271. (f)Bestmann,
H. J.; Schobert, T. Angew. Chem. Int. Ed. Engl. 1985, 24,
790. (g) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25,
508. (h) Neyer, G.; Achatz, J.; Panzer, B.; Ugi, I.
References
(1) For reviews see: (a) Schank, K. In The Chemistry of
Sulphones and Sulfoxides; Patai, S.; Rappoport, Z.; Stirling,
C. J. M., Eds.; Wiley: Chichester, 1988, 165–231.
(b) Schank, K. In Syntheses of Sulphones, Sulphoxides and
Cyclic Sulphides; Patai, S.; Rappoport, Z., Eds.; Wiley:
Chichester, 1994, 1–67. (c) Schank, K.; Schott, N. In
Syntheses of Sulphones, Sulphoxides and Cyclic Sulphides;
Patai, S.; Rappoport, Z., Eds.; Wiley: Chichester, 1994, 69–
108.
(2) See, For Example: (a) Backer, H. J.; Stevens, W.; Dost, N.
Recl. Trav. Chim. Pays-Bas 1948, 67, 456. (b) Backer, H.
J.; De Jong, G. J. Recl. Trav. Chim. Pays-Bas 1951, 70 ,
377. (c) Edwards, D.; Stenlake, J. B. J. Chem. Soc. 1956,
3892. (d) Bavin, P. M. G. Can. J. Chem. 1962, 27, 3483.
(e) Raper, A. H.; Rothstein, E. J. Chem. Soc. 1963, 2463.
(f) Block, E.; Ahmad, S.; Catalfamo, J. L.; Jain, M. K.;
Anitz-Castro, R. J. Am. Chem. Soc. 1986, 108, 7045.
(g) Ali, M. E.; Kardouche, N. G.; Owen, L. N. J Chem. Soc.,
Perkin Trans.1 1975, 748. (h) Kosugi, K.; Anisimov, A. V.;
Yamamoto, H.; Yamashiro, R.; Shirai, K.; Kumamoto, T.
Chem. Lett. 1981, 1341. (i) Kanematsu, K.; Kinoyama, I. J.
Chem. Soc., Chem Commun. 1992, 735. (j) Yeo, S.-K.;
Shiro, M.; Kanematsu, K. J. Org. Chem. 1994, 59, 1621.
(k) Cao, X.-P.; Chan, T.-L.; Chow, H.-F.; Tu, J. J. Chem.
Soc., Chem. Commun. 1995, 1297. (l) Miller, J. F.; Termin,
A.; Koch, K.; Piscopio, A. D. J. Org. Chem. 1998, 63, 3158.
(3) Bradamante, S.; Maiorana, S.; Pagani, G. J. Chem. Soc.,
Perkin Trans. 1 1972, 282.
(4) (a) Rothstein, E. J. Chem. Soc. 1934, 684. (b) Näf, F.;
Decorzant, R.; Escher, S. D. Tetrahedron Lett. 1982, 23,
5043.
(5) See, For Example: (a) Baudin, J. B.; Julia, S. Bull. Soc.
Chim. Fr. 1995, 132, 196. (b) Braverman, S.; Pechenick, T.;
Zafrani, Y.; Gottlieb, H. E. Tetrahedron Lett. 2000, 41,
2675. (c) Braverman, S.; Pechenick, T.; Zafrani, Y.
Tetrahedron Lett. 2001, 41, 1391.
(6) See, For Example: Block, E.; Aslam, M.; Eswarakrishnan,
V.; Gebreyes, K.; Hutchinson, J.; Iyer, R.; Laffitte, J.-A.;
Wall, A. J. Am. Chem. Soc. 1986, 108, 4568; and references
cited therein.
(7) Klein, H. S. J. Chem. Soc., Chem. Commun. 1968, 7, 377.
(8) (a) Gibson, H. W.; McKenzie, D. A. J. Org. Chem. 1970, 35,
2994. (b) Jarvis, W. F.; Dittmer, D. C. J. Org. Chem. 1983,
48, 2784. See also: (c)Keim, W.; Herwig, J.; Pelzer, G. J.
Org. Chem. 1997, 62, 422.
Heterocycles 1990, 30, 863. (i) Ryu, I.; Yamazaki, H.;
Ogawa, A.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1993,
115, 1187. (j) Doemling, A.; Ugi, I. Angew. Chem., Int. Ed.
Engl. 1993, 32, 563. (k) Ugi, I.; Domling, A.; Horl, W.
Endeavour 1994, 18, 115. (l) Ryu, I.; Sonoda, N. Angew.
Chem., Int. Ed. Engl. 1996, 35, 1050. (m) Montalbetti, C.;
Savignac, M.; Genêt, J.-P.; Roulet, J.-M.; Vogel, P.
Tetrahedron Lett. 1996, 37, 2225. (n) Ojima, I.;
Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996,
96, 635. (o) Annunziata, R.; Cinquini, M.; Cozzi, F.;
Molteni, V.; Schupp, O. Tetrahedron 1997, 53, 9715.
(p) Ghosez, L.; Jnoff, E.; Bayard, P.; Sainte, F.;
Beaudegnies, R. Tetrahedron 1999, 55, 3387. (q) Beller,
M.; Eckert, M.; Moradi, W. A.; Neumann, H. Angew. Chem.,
Int. Ed. 1999, 38, 1454. (r) Oertel, K.; Zeck, G.; Kunz, H.
Angew. Chem., Int. Ed. 2000, 39, 1431. (s) Maison, W.;
Lutzen, A.; Korsten, M.; Schlemminger, I.; Westerhoff, O.;
Saak, W.; Martens, J. J. Chem. Soc., Perkin Trans. 1 2000,
1867. (t) Maison, W.; Schlemminger, I.; Westerhoff, O.;
Martens, J. Bioorg. Med. Chem. 2000, 8, 1343. (u) Ugi, I.;
Domling, A. J. Heterocycl. Chem. 2000, 37, 647. (v) Sun,
X.; Janvier, P.; Zhao, G.; Bienayme, H.; Zhu, J. Org. Lett.
2001, 3, 877. (w) Ugi, I. Pure Appl. Chem. 2001, 73, 187.
(14) To our knowledge the ene-reaction of sulfur dioxide with
silyl enol ether derived from ketone had never been reported.
(15) (a) Hiscock, S. D.; Isaacs, N. S.; King, M. D.; Sue, R. E.;
White, R. H.; Young, D. J. Tetrahedron Lett. 1997, 38,
4493. (b) King, M. D.; Sue, R. E.; White, R. H.; Young, D.
J. J. Org. Chem. 1995, 60, 7166. (c) Fong, C. W.; Kitching,
W. J. Organomet. Chem. 1970, 22, 95.
(16) (a) Skattebol, L.; Boulette, B.; Solomon, S. J. Org. Chem.
1968, 33, 548. See also: (b)Stirling, C. J. M. J. Chem. Soc.
1964, 5856.
(17) D’Silva, T. D. J.; Lopes, A.; Jones, R. L.; Singhawangcha,
S.; Chan, J. K. J. Org. Chem. 1986, 51, 3781.
(18) (a) Wichterle, O.; Rocek, J. Collect. Czeck. Chem. Commun.
1954, 19, 282; Chem. Abstr. 1955, 49, 1053. (b) Kresze, G.;
Maschpe, A.; Albrecht, R.; Bederke, K.; Patzschke, H. P.;
Smalla, H.; Trede, A. Angew. Chem. 1962, 74, 135.
(c) Rogic, M. M.; Masilamani, D. J. Am. Chem. Soc. 1977,
99, 5219. (d) Bravermann, S. In The Chemistry of the
Sulfinic Acid, Esters and their Derivatives; Patai, S.;
(9) (a) Grieco, P. A.; Boxler, D. Synth. Commun. 1975, 315.
(b) Sergeev, V. N.; Shipov, A.-G.; Zaitseva, G.-S.; Baukov,
Yu. Zh. Obshch. Khim. 1979, 2753; Chem. Abstr. 1980, 92,
146839.
(10) For the nucleophilic reactions of sulfinates, see: Okuyama,
T. In The Chemistry of Sulphinic Acids, Esters and their
Derivatives; Patai, S., Ed.; Wiley: Chichester, 1990, 639–
662.
(11) For other one-pot synthesis of -keto sulfones, see, e.g.
(a) Polakovicova, D.; Jurasek, A.; Kvasnicka, V. Collect.
Czech. Chem. Commun. 1982, 47, 617. (b) Alvarez, I. C.;
Cuervo Rodriguez, R.; Fernandez Monreal, M. C.; García
Navarro, F. J.; Martín Tesorero, J. J. Org. Chem. 1989, 54,
5620. (c) Jacobs, H. K.; Gopalan, A. S. J. Org. Chem. 1994,
59, 2014. (d) Cao, S. Liaoning Shifan Daxue Xuebao, Ziran
Kexueban 1997, 20, 232; Chem. Abstr. 1998, 129, 2022722.
Synthesis 2002, No. 2, 225–231 ISSN 0039-7881 © Thieme Stuttgart · New York