Asymmetric Oxidative Dimerization of the Enolates of N-[Bis(methylthio)methylene]- and N-(Diphenylmethylene)glycine Esters

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2478-2482

  Alvarez Ibarra, Carlos ^a   Csákÿ, Aurelio G ^a   Colmenero, Belén ^a   Quiroga, M Luz ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000652518     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962116c     Document Type: Article

References (46)

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17. The stereochemieal descriptors E and Z are used in this context as recommended by Evans. See: Evans, D. A. In Asymmetric Synthesis; Morrison, J. D., Ed., Academic Press: New York, 1984; Vol. 3, p 11.
18. A mixture 65:35 of 3b-I and 3b-II was transformed into a mixture 65:35 of 4a-I and 4a-II.
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20. The absolute stereochemistry and the optical purity of the reaction of Id was deduced by measuring the optical rotations of 5-I and 5-II and comparing the physical and spectroscopic properties with the known compounds. See: (a) McKennis H., Jr.; Yard, A. S. J. Org. Chem. 1958, 23, 980. (b) Hochstein, F. A. J. Org. Chem. 1959, 24, 679.
21. The absolute stereochemistry and the optical purity of the reaction of Id was deduced by measuring the optical rotations of 5-I and 5-II and comparing the physical and spectroscopic properties with the known compounds. See: (a) McKennis H., Jr.; Yard, A. S. J. Org. Chem. 1958, 23, 980. (b) Hochstein, F. A. J. Org. Chem. 1959, 24, 679.
22. Rathke, M. W.; Lindert, A. Tetrahedron Lett. 1971, 3995. α-Halogenated esters give consecutive reactions when generated in the presence of an excess of enolate.
23. Kochi, J. K. In Comprehensive Organic Synthesis; Trost, B. M., Ed., Pergamon Press: Oxford 1991; Vol. 7, p 842.
24. A thermodynamical reaction pathway for the oxidative dimerization of the lithium enolates in the absence of DMPU is ruled out on the basis of the isomerization of a 98:02 mixture of 3b-I and 3b-II to a mixture 45:55. See Results.
25. 7b obtained the same relative configuration in the dimerization of alicyclic esters independently of the E or Z geometry of the starting enolate. However DMPU was present in the reaction medium in the coupling step. DMPU is known to promote formation of Z enolates: (a) Helmchen, G., Selim, A.; Dorsch, D.; Taufer, I. Tetrahedron Left. 1983, 24, 3213. (b) Helmchen, G.; Wierzchowski, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 60.
26. 7b obtained the same relative configuration in the dimerization of alicyclic esters independently of the E or Z geometry of the starting enolate. However DMPU was present in the reaction medium in the coupling step. DMPU is known to promote formation of Z enolates: (a) Helmchen, G., Selim, A.; Dorsch, D.; Taufer, I. Tetrahedron Left. 1983, 24, 3213. (b) Helmchen, G.; Wierzchowski, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 60.
27. 2 reaction between enolates 2 and the corresponding α-iodide is ruled out on the basis of the inhibition of the oxidative dimerization in the presence of benzophenone. This results reveals the participation of radical species. See Results.
28. (a) Ireland, R. E.; Mueller, R. H.; Williard, A. K. J. Am. Chem. Soc. 1976, 98, 2868.
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30. LDA is a dimer in THF. See: (a) Seebach, D.; Häsigg, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308. (b) Bauer, W.; Clark, T.; Schleyer, P. von R. J. Am. Chem. Soc. 1987, 109, 970.
31. LDA is a dimer in THF. See: (a) Seebach, D.; Häsigg, R.; Gabriel, J. Helv. Chim. Acta 1983, 66, 308. (b) Bauer, W.; Clark, T.; Schleyer, P. von R. J. Am. Chem. Soc. 1987, 109, 970.
32. tBuLi is monomeric in THF. See: Bauer, W.; Winchester, W. R.; Schleyer, P. von R. Organometallics 1987, 6, 2371. For the extension of Ireland's model to alkyllithiums see: (a) Solladié-Cavallo, A.; Csákÿ, A. G. J. Org. Chem. 1994, 59, 2585. (b) Solladié-Cavallo, A. Csáky, A. G.; Gantz, I.; Suffert, J. J. Org. Chem. 1994, 59, 5343.
33. tBuLi is monomeric in THF. See: Bauer, W.; Winchester, W. R.; Schleyer, P. von R. Organometallics 1987, 6, 2371. For the extension of Ireland's model to alkyllithiums see: (a) Solladié-Cavallo, A.; Csákÿ, A. G. J. Org. Chem. 1994, 59, 2585. (b) Solladié-Cavallo, A. Csáky, A. G.; Gantz, I.; Suffert, J. J. Org. Chem. 1994, 59, 5343.
34. tBuLi is monomeric in THF. See: Bauer, W.; Winchester, W. R.; Schleyer, P. von R. Organometallics 1987, 6, 2371. For the extension of Ireland's model to alkyllithiums see: (a) Solladié-Cavallo, A.; Csákÿ, A. G. J. Org. Chem. 1994, 59, 2585. (b) Solladié-Cavallo, A. Csáky, A. G.; Gantz, I.; Suffert, J. J. Org. Chem. 1994, 59, 5343.
35. Hindered esters and amides give Z-enolates upon deprotonation under kinetic conditions. See for example: Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1.
36. For the use of (-)-8-phenylmenthol as chiral inducer see: (a) Comins, D. L.; Guerra-Weltzien, L.; Salvador, J. M. Synlett 1994, 972 and references cited therein. In connection with π-facial diastereoselectivity in 8-phenylmenthyl derivatives, there is theoretical and spectroscopic evidence of a π-π stabilizing interaction of the conformer which has a cis relative disposition of the aromatic ring and the conjugated system of the side chain. See: (a) Solladié-Cavallo, A.; Khiar, N. Tetrahedron Lett. 1988, 29, 2189. (b) Denmark, S. E.; Schnute, M. E.; Senayake, C. B. W. J. Org. Chem. 1993, 58, 1859. (c) Maddaluno, J. F.; Gresh, N.; Giessner-Prettre, C. J. Org. Chem. 1994, 59, 793. (d) Shida, N.; Kabuto, C.; Niwa, T.; Ebata, T.; Yamamoto, Y. J. Org. Chem. 1994, 59, 4068.
37. For the use of (-)-8-phenylmenthol as chiral inducer see: (a) Comins, D. L.; Guerra-Weltzien, L.; Salvador, J. M. Synlett 1994, 972 and references cited therein. In connection with π-facial diastereoselectivity in 8-phenylmenthyl derivatives, there is theoretical and spectroscopic evidence of a π-π stabilizing interaction of the conformer which has a cis relative disposition of the aromatic ring and the conjugated system of the side chain. See: (a) Solladié-Cavallo, A.; Khiar, N. Tetrahedron Lett. 1988, 29, 2189. (b) Denmark, S. E.; Schnute, M. E.; Senayake, C. B. W. J. Org. Chem. 1993, 58, 1859. (c) Maddaluno, J. F.; Gresh, N.; Giessner-Prettre, C. J. Org. Chem. 1994, 59, 793. (d) Shida, N.; Kabuto, C.; Niwa, T.; Ebata, T.; Yamamoto, Y. J. Org. Chem. 1994, 59, 4068.
38. For the use of (-)-8-phenylmenthol as chiral inducer see: (a) Comins, D. L.; Guerra-Weltzien, L.; Salvador, J. M. Synlett 1994, 972 and references cited therein. In connection with π-facial diastereoselectivity in 8-phenylmenthyl derivatives, there is theoretical and spectroscopic evidence of a π-π stabilizing interaction of the conformer which has a cis relative disposition of the aromatic ring and the conjugated system of the side chain. See: (a) Solladié-Cavallo, A.; Khiar, N. Tetrahedron Lett. 1988, 29, 2189. (b) Denmark, S. E.; Schnute, M. E.; Senayake, C. B. W. J. Org. Chem. 1993, 58, 1859. (c) Maddaluno, J. F.; Gresh, N.; Giessner-Prettre, C. J. Org. Chem. 1994, 59, 793. (d) Shida, N.; Kabuto, C.; Niwa, T.; Ebata, T.; Yamamoto, Y. J. Org. Chem. 1994, 59, 4068.
39. For the use of (-)-8-phenylmenthol as chiral inducer see: (a) Comins, D. L.; Guerra-Weltzien, L.; Salvador, J. M. Synlett 1994, 972 and references cited therein. In connection with π-facial diastereoselectivity in 8-phenylmenthyl derivatives, there is theoretical and spectroscopic evidence of a π-π stabilizing interaction of the conformer which has a cis relative disposition of the aromatic ring and the conjugated system of the side chain. See: (a) Solladié-Cavallo, A.; Khiar, N. Tetrahedron Lett. 1988, 29, 2189. (b) Denmark, S. E.; Schnute, M. E.; Senayake, C. B. W. J. Org. Chem. 1993, 58, 1859. (c) Maddaluno, J. F.; Gresh, N.; Giessner-Prettre, C. J. Org. Chem. 1994, 59, 793. (d) Shida, N.; Kabuto, C.; Niwa, T.; Ebata, T.; Yamamoto, Y. J. Org. Chem. 1994, 59, 4068.
40. For the use of (-)-8-phenylmenthol as chiral inducer see: (a) Comins, D. L.; Guerra-Weltzien, L.; Salvador, J. M. Synlett 1994, 972 and references cited therein. In connection with π-facial diastereoselectivity in 8-phenylmenthyl derivatives, there is theoretical and spectroscopic evidence of a π-π stabilizing interaction of the conformer which has a cis relative disposition of the aromatic ring and the conjugated system of the side chain. See: (a) Solladié-Cavallo, A.; Khiar, N. Tetrahedron Lett. 1988, 29, 2189. (b) Denmark, S. E.; Schnute, M. E.; Senayake, C. B. W. J. Org. Chem. 1993, 58, 1859. (c) Maddaluno, J. F.; Gresh, N.; Giessner-Prettre, C. J. Org. Chem. 1994, 59, 793. (d) Shida, N.; Kabuto, C.; Niwa, T.; Ebata, T.; Yamamoto, Y. J. Org. Chem. 1994, 59, 4068.
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