The tert-butylsulfinyl group as a highly efficient chiral auxiliary in asymmetric Pauson-Khand reactions [4]

Journal of the American Chemical Society

Volumn 121, Issue 32, 1999, Pages 7411-7412

  Adrio, Javier ^a   Carretero, Juan C ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

SULFINIC ACID DERIVATIVE;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0033581173     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990546p     Document Type: Letter

References (32)

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2. For recent reviews, see: (a) Geis, O.; Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911. (b) Schore, N. E. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Elsevier: New York, 1995; Vol. 12, p 703.
3. See, for instance: (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse Tetrahedron Lett. 1998, 39, 7637 (and 7641). (b) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782 and references therein.
4. See, for instance: (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse Tetrahedron Lett. 1998, 39, 7637 (and 7641). (b) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782 and references therein.
5. See, for instance: (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse Tetrahedron Lett. 1998, 39, 7637 (and 7641). (b) Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384. Sugihara, T.; Yamaguchi, M. J. Am. Chem. Soc. 1998, 120, 10782 and references therein.
6. Complete asymmetric inductions have been reported in the PK reaction of alkynoyl derivatives of Oppolzer's sultam with norbornadiene, see: Fonquerna, S.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Am. Chem. Soc. 1997, 119, 10225. See, also: Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes- Génisson, V.; Greene, A. E.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037 and references therein.
7. Complete asymmetric inductions have been reported in the PK reaction of alkynoyl derivatives of Oppolzer's sultam with norbornadiene, see: Fonquerna, S.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Am. Chem. Soc. 1997, 119, 10225. See, also: Verdaguer, X.; Vázquez, J.; Fuster, G.; Bernardes-Génisson, V.; Greene, A. E.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1998, 63, 7037 and references therein.
8. (a) The best diastereoselectivities (up to 10:1 isomer ratio) have been reported from alkenyl ethers derived from optically pure trans-2-phenylcyclohexanol, see: Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388. See, also: (b) Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E.; Piniella, J. F.; Alvarez-Larena, A. J. Organomet. Chem. 1992, 433, 305. (c) Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E.; Alvarez- Larena, A.; Piniella, J. F J. Org. Chem. 1996, 61, 9016.
9. (a) The best diastereoselectivities (up to 10:1 isomer ratio) have been reported from alkenyl ethers derived from optically pure trans-2-phenylcyclohexanol, see: Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388. See, also: (b) Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E.; Piniella, J. F.; Alvarez-Larena, A. J. Organomet. Chem. 1992, 433, 305. (c) Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E.; Alvarez- Larena, A.; Piniella, J. F J. Org. Chem. 1996, 61, 9016.
10. (a) The best diastereoselectivities (up to 10:1 isomer ratio) have been reported from alkenyl ethers derived from optically pure trans-2-phenylcyclohexanol, see: Castro, J.; Sörensen, H.; Riera, A.; Morin, C.; Moyano, A.; Pericàs, M. A.; Greene, A. E. J. Am. Chem. Soc. 1990, 112, 9388. See, also: (b) Verdaguer, X.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E.; Piniella, J. F.; Alvarez-Larena, A. J. Organomet. Chem. 1992, 433, 305. Castro, J.; Moyano, A.; Pericàs, M. A.; Riera, A.; Greene, A. E.; Alvarez-Larena, A.; Piniella, J. F J. Org. Chem. 1996, 61, 9016.
11. (a) Brunner, H.; Niedernhuber, A. Tetrahedron: Asymmetry 1990, 1, 711.
12. (b) Hay, A. M.; Kerr, W. J.; Kirk, G. G.; Middlemiss, D. Organometallics 1995, 14, 4986.
13. (c) Park, H.-J.; Lee, B. Y.; Kang, Y. K.; Chung, Y. K. Organometallics 1995, 14, 3104.
14. (a) Kerr, W. J.; Kirk, G. G.; Middlemiss, D. Synlett 1995, 1085.
15. (b) Derdau, V.; Laschat, S.; Jones, P. G. Heterocycles 1998, 48, 1445. For an outstanding catalytic and enantioselective titanocene-catalyzed cyclocarbonylation of enynes, see: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688.
16. (b) Derdau, V.; Laschat, S.; Jones, P. G. Heterocycles 1998, 48, 1445. For an outstanding catalytic and enantioselective titanocene-catalyzed cyclocarbonylation of enynes, see: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688.
17. For a review, see: Carreño, C. Chem. Rev. 1995, 95, 1717.
18. For sulfoxides as chiral auxiliaries in transition-metal-catalyzed reactions, see: (a) Paley, R. S.; Rubio, M. B.; Fernández de la Pradilla, R.; Dorado, R.; Hundal, G.; Martínez-Ripoll, M. Organometallics 1996, 15, 4672. (b) Villar, J. M.; Delgado, A.; Llebaria, A.; Moretó, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (d) Chaigne, F.; Gotteland, J.-P.; Malacria, M. Tetrahedron Lett. 1989, 30, 1989. For a recent report on the use of sulfoxides as chiral ligands, see: Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715 and references therein.
19. For sulfoxides as chiral auxiliaries in transition-metal-catalyzed reactions, see: (a) Paley, R. S.; Rubio, M. B.; Fernández de la Pradilla, R.; Dorado, R.; Hundal, G.; Martínez-Ripoll, M. Organometallics 1996, 15, 4672. (b) Villar, J. M.; Delgado, A.; Llebaria, A.; Moretó, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (d) Chaigne, F.; Gotteland, J.-P.; Malacria, M. Tetrahedron Lett. 1989, 30, 1989. For a recent report on the use of sulfoxides as chiral ligands, see: Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715 and references therein.
20. For sulfoxides as chiral auxiliaries in transition-metal-catalyzed reactions, see: (a) Paley, R. S.; Rubio, M. B.; Fernández de la Pradilla, R.; Dorado, R.; Hundal, G.; Martínez-Ripoll, M. Organometallics 1996, 15, 4672. (b) Villar, J. M.; Delgado, A.; Llebaria, A.; Moretó, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (d) Chaigne, F.; Gotteland, J.-P.; Malacria, M. Tetrahedron Lett. 1989, 30, 1989. For a recent report on the use of sulfoxides as chiral ligands, see: Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715 and references therein.
21. For sulfoxides as chiral auxiliaries in transition-metal-catalyzed reactions, see: (a) Paley, R. S.; Rubio, M. B.; Fernández de la Pradilla, R.; Dorado, R.; Hundal, G.; Martínez-Ripoll, M. Organometallics 1996, 15, 4672. (b) Villar, J. M.; Delgado, A.; Llebaria, A.; Moretó, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. Chaigne, F.; Gotteland, J.-P.; Malacria, M. Tetrahedron Lett. 1989, 30, 1989. For a recent report on the use of sulfoxides as chiral ligands, see: Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715 and references therein.
22. For sulfoxides as chiral auxiliaries in transition-metal-catalyzed reactions, see: (a) Paley, R. S.; Rubio, M. B.; Fernández de la Pradilla, R.; Dorado, R.; Hundal, G.; Martínez-Ripoll, M. Organometallics 1996, 15, 4672. (b) Villar, J. M.; Delgado, A.; Llebaria, A.; Moretó, J. M. Tetrahedron: Asymmetry 1995, 6, 665. Hiroi, K.; Arinaga, Y. Tetrahedron Lett. 1994, 35, 153. (d) Chaigne, F.; Gotteland, J.-P.; Malacria, M. Tetrahedron Lett. 1989, 30, 1989. For a recent report on the use of sulfoxides as chiral ligands, see: Hiroi, K.; Suzuki, Y.; Kawagishi, R. Tetrahedron Lett. 1999, 40, 715 and references therein.
23. Díaz Buezo, N.; Alonso, I.; Carretero, J. C. J. Am. Chem. Soc. 1998, 120, 7129.
24. During the editorial review process several examples of intermolecular PK reactions of optically pure alkynyl p-tolyl sulfoxides have been published: Montenegro, E.; Moyano, A.; Pericàs, M. A.; Riera, A.; Alvarez-Larena, A.; Piniella, J.-F. Tetrahedron: Asymmetry 1999, 10, 457.
25. 3N; then DBU). Both methods afforded cis + trans mixtures of olefins (the trans α,β-sulfoxide as the major one) which were easily separated by flash chromatography. Similarly, (R)-1 was prepared from the readily available (R)-methyl p-tolyl sulfoxide (Solladié, G.; Hunt, J.; Girardin, A. Synthesis 1987, 13).
26. (a) Smit, W. A.; Gybin, A. S.; Shashkov, A. S.; Strychkov, Y. T.; Kizmina, L. G.; Mikaelian, G. S.; Caple, R.; Swanson, E. D. Tetrahedron Lett. 1986, 27, 1241.
27. (b) Khand, I. U.; Pauson, P. L. Heterocycles 1978, 11, 59. To the best of our knowledge, only some specific alkynyl enones have led to successful results in cobalt-catalyzed PK reactions, see: (c) Veretenov, A. L.; Smit, W. A.; Vorontsova, L. G.; Kurella, M. G.; Caple, R.; Gybin, A. S. Tetrahedron Lett. 1991, 32, 2109. See, also: (d) Costa, M.; Mor, A. Tetrahedron Lett. 1995, 36, 2867.
28. (b) Khand, I. U.; Pauson, P. L. Heterocycles 1978, 11, 59. To the best of our knowledge, only some specific alkynyl enones have led to successful results in cobalt-catalyzed PK reactions, see: (c) Veretenov, A. L.; Smit, W. A.; Vorontsova, L. G.; Kurella, M. G.; Caple, R.; Gybin, A. S. Tetrahedron Lett. 1991, 32, 2109. See, also: (d) Costa, M.; Mor, A. Tetrahedron Lett. 1995, 36, 2867.
29. (b) Khand, I. U.; Pauson, P. L. Heterocycles 1978, 11, 59. To the best of our knowledge, only some specific alkynyl enones have led to successful results in cobalt-catalyzed PK reactions, see: (c) Veretenov, A. L.; Smit, W. A.; Vorontsova, L. G.; Kurella, M. G.; Caple, R.; Gybin, A. S. Tetrahedron Lett. 1991, 32, 2109. See, also: (d) Costa, M.; Mor, A. Tetrahedron Lett. 1995, 36, 2867.
30. The configuration of A and B isomers was established first by X-ray difraction of enantiopure 6A (see Supporting Information) and confirmed afterwards by chemical correlations: (a) The oxidation of either 4A or 4B with MCPBA led to the same sulfone.
31. 4Cl, THF) of the enantiopure major isomer 4A obtained from the PK reaction of (R)-1, and that of 6A obtained from (S)-3, led to opposite enantiomers of enone 21a (Table 3).
32. 19 (Table 3).