Highly stereoselective benzylation of N-sulfinylketimines

Journal of the American Chemical Society

Volumn 127, Issue 37, 2005, Pages 13048-13054

  García Ruano, José Luis ^a   Alemán, José ^a   Parra, Alejandro ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; ISOMERS; NEGATIVE IONS; NITROGEN; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

BENZYLATION; N-SULFINYL KETIMINES; SUFINYL GROUPS; T-ALKYLAMINES;

ORGANIC COMPOUNDS;

2 (4 TOLYLSULFINYL)BENZYL ALCOHOL; 2 (4 TOLYLSULFINYL)ETHYLBENZENE; ALIPHATIC AMINE; AMINOALCOHOL; BENZYL ALCOHOL DERIVATIVE; CARBON; ETHYLBENZENE; IMINE; N SULFINYLKETIMINE DERIVATIVE; NITROGEN; SULFOXIDE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; DESULFINYLATION; DIASTEREOISOMER; EPIMER; OPTICAL ROTATION; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

ALKYLATION; IMINES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFUR COMPOUNDS;

EID: 25144447345     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0515203     Document Type: Article

References (57)

1. (a) Volkmann, R. A. In Comprehensive Organic Synthesis; Schreiber, S. L., Ed.; Pergamon Press: Oxford, 1991; Vol. 1, Chapter 1.12, p 355.
2. (b) Risch, N.; Arend, M. In Stereoselective Synthesis (Houben-Weyl); Helmechen, G., Hoffmann, R. W., Mulzer, J., Schauman, E., Eds.; Georg Thieme Verlag: Stutgart, 1995; E21b, D.1.4, p 1833.
3. (c) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
4. Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555.
5. (a) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13 and references therein.
6. (b) Zhou, P.; Chen, B.-C.; Davis, F. A. Tetrahedron 2004, 50, 8003.
7. (c) Davis, F. A.; Nolt, M. B.; Wu, Y.; Prasad, K. R.; Li, D.; Yang, B.; Bowen, K.; Lee, S. H.; Eardley, J. H. J. Org. Chem. 2005, 70, 2184.
8. (d) Davis, F. A.; Yang, B. J. Am. Chem. Soc. 2005, 127, 8398-8407.
9. (a) Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. J. Am. Chem. Soc. 1998, 120, 8011.
10. (b) Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Org. Chem. 1999, 64, 1278.
11. (c) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984 and references therein.
12. (d) McMahon, J. P.; Ellman, J. A. Org. Lett. 2004, 6, 1645.
13. (e) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2004, 6, 3621.
14. (f) Kochi, T.; Ellman, J. A. J. Am. Chem. Soc. 2004, 126, 15652.
15. (g) Weix, D. J.; Shi, Y.; Ellman, J. A. J. Am. Chem. Soc. 2005, 127, 1092.
16. (a) Stork, G.; Dowd, S. R. J. Am. Chem. Soc. 1963, 85, 2178.
17. (b) Hua, D. H.; Miao, S. W.; Chen, J. S.; Iguchi, S. J. Org. Chem. 1991, 56, 4.
18. (c) Hua, D. H.; Lagneau, N.; Wang, H.: Chen. J. S. Tetrahedron: Asymmetrv, 1995, 6, 349.
19. (a) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207.
20. (b) Spero, D. M.; Kapadia, S. R. J. Org. Chem. 1997, 62, 5537.
21. (c) Steining, A. G.; Spero, M. D. J. Org. Chem. 1999, 64, 2406.
22. Cogan, D. A.; Liu, G.; Ellman, J. Tetrahedron 1999, 55, 8883.
23. (a) García Ruano, J. L.; Alcudia, A.; Prado, M.; Barros, D.; Maestro, M. C.; Fernández, I. J. Org. Chem. 2000, 65, 2856.
24. (a) García Ruano, J. L.; Alemán, J.; Soriano, J. F. Org. Lett. 2003, 5, 677.
25. (b) García Ruano, J. L.; Alemán, J. Org. Lett. 2003, 5, 4513.
26. (a) Moreau, P.; Essiz, M.; Merour, J.-Y.; Bouzard, D. Tetrahedron: Asymmetry 1997, 8, 591.
27. (b) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
28. (c) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396.
29. (d) Davis, F. A.; Mohanty, P. K.; Burns, D. M.; Andemichael, Y. W. Org, Lett. 2000, 2, 3902.
30. (e) Davis, F. A.; Andemichael, Y. W. Tetrahedron Lett. 1999, 49, 3099.
31. (f) Davis, F. A.; Pradyudmna, K. M. J. Org. Chem. 2002, 67, 1290.
32. García Ruano, J. L.; Alemán, J.; Prado, M.; Fernandez, I. J. Org. Chem. 2004, 69, 4454.
33. Garcia Ruano, J. L.; Alemán, J.; Cid, M. B.: Parra, A. Org. Lett. 2005, 6, 179.
34. The obtained results in reaction of (5)-5 and (5)-3 suggest that reaction rates for enolization and nucleophilic addition processes must be similar.
35. A similar situation had been found in reactions of (5)-5 with aldimines (ref 9) but being the reagents with the same configuration at sulphur those conforming the matched pair.
36. It suggests that 15a and 16a, formed from 9a, must be epimers at the aminic carbon.
37. This result it was obtained in the case of the carbanion with ketones. See ref 19.
38. 3-A1 and decomposes into the corresponding ketone and N-sulfinamide.
39. Epimerization at chiral centers in the hydrogenolysis of the C-S bonds with Ra-Ni has been observed in some cases. See: García Ruano, J. L.; Paredes, C. G.; Hamdouchi, C. Tetrahedron: Asymmetry 1999, 10, 2935 and references therein.
40. García Ruano, J. L.; Carreño, M. C.; Toledo, M. A.; Aguirre, J. M.; Aranda, M.; Fischer, J. Angew. Chem., Int. Ed. 2000, 39, 2736.
41. These transition states would not be negligible for N-sulfinylaldimines and would explain the differences in their behaviour with respect to the N-sulfinylketimines.
42. Yuki, Y.; Saigo, K.; Tachibana, K.; Hasegava, M. Chem. Lett. 1986, 1347.
43. Relevant bioactive naturally occurring amino alcohols: (a) Nikolau, K. C.; Mitchel, H. J.; van Delft, F. L.; Rubsam, F.; Rodríguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871.
44. (b) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1998, 38, 750.
45. (c) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. 1998, 38, 1532.
46. (d) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
47. Recent reviews: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
48. (b) Bloch, R. Chem. Rev. 1998, 98, 1407.
49. (c) Reetz, M. T. Chem. Rev. 1999, 99, 1121.
50. (d) Comprehensive Asymmetric Catalyst; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999.
51. (e) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; VCH: New York, 2000.
52. (f) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
53. (g) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981.
54. (h) Tang, Z.; Jiang, F.; Yu, L.-T.; Xin, C.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
55. Fuller, A. A.; Chen, B.; Minter, A.; Mapp. A. Synlett 2004, 8, 1409.
56. Annunziata, R.; Cinquini, M.; Cozzi, F. J. Chem. Soc., Perkin Trans, 1 1982, 2, 339.
57. Davis, F. A.; Seung, L.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 65, 8704.