Asymmetric synthesis of acyclic 1,3-amino alcohols by reduction of N-sulfinyl β-amino ketones. Formal synthesis of (-)-pinidinol and (+)- epipinidinol

Journal of Organic Chemistry

Volumn 73, Issue 24, 2008, Pages 9619-9626

  Davis, Franklin A ^a   Gaspari, Paul M ^a   Nolt, Brad M ^a   Xu, Peng ^a  

^a Temple University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS; ASYMMETRIC SYNTHESES; CASCADE REACTIONS; CHEMICAL EQUATIONS; FORMAL SYNTHESES; PIPERIDINE RINGS; STEREOSELECTIVE REDUCTIONS;

ALCOHOLS; AMINATION; CHEMICAL REACTIONS; ELECTRON TRANSITIONS; KETONES; ORGANIC COMPOUNDS; SILANES; SYNTHESIS (CHEMICAL);

AMINES;

AMINO ALCOHOLS; INDICATORS AND REAGENTS; KETONES; OXIDATION-REDUCTION; PIPERIDINES; STEREOISOMERISM;

EID: 58049193072     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801653c     Document Type: Article

References (52)

1. (a) Kempf, D. J.; Marsh, K. C.; Denissen, J. F.; McDonald, E.; Vasavanonda, S.; Flentge, C. A.; Green, B. E.; Fino, L.; Park, C. H.; Kong, X.-P.; Wideburg, N. E.; Saldivar, A.; Ruiz, L.; Kati, W. M.; Sham, H. L.; Robins, T.; Stewart, K. D.; Hsu, A.; Plattner, J. J.; Leonard, J. M.; Norbeck, D. W. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 2484.
2. (b) Haight, A. R.; Stuk, T. L.; Allen, M. S.; Bhagavatula, L.; Fitzgerald, M.; Hannick, S. M.; Kerdesky, F. A. J.; Menzia, J. A.; Parekh, S. I.; Robbins, T. A.; Scarpetti, D.; Tien, J.-H. J. Org. Process Res. Dev. 1999, 3, 94.
3. (c) Sham, H. L.; Zhao, C.; Li, L.; Betebenner, D. A.; Saldivar, A.; Vasavanonda, S.; Kempf, D. J.; Plattner, J. J.; Norbeck, D. W. Bioorg. Med. Chem. Lett. 2002, 12, 3101.
4. Shi, Z.; Harrison, B. A.; Verdine, G. L. Org. Lett. 2003, 5, 633.
5. (a) Kondo, S.; Shibahara, S.; Takahashi, S.; Maeda, K.; Umezawa, H.; Ohno, M. J. Am. Chem. Soc. 1971, 93, 6305.
6. (b) Raju, B.; Mortell, K.; Anandan, S.; O'Dowd, H.; Gao, H.; Gomez, M.; Hackbarth, C.; Wu, C.; Wang, W.; Yuan, Z.; White, R.; Trias, J.; Patel, D. V. Bioorg. Med. Chem. Lett. 2003, 13, 2413.
7. (a) Carlier, P. R.; Lo, M. M.-C.; Lo, P. C -K.; Richelson, E.; Tatsumi, M.; Reynolds, I. J.; Sharma, T. A. Bioorg. Med. Chem. Lett. 1998, 8, 487-492.
8. Nechev, L. V.; Kozedov, I.; Harris, C. M.; Harris, T. M. Chem. Res. Toxicol. 2001, 14, 1506.
9. Bates, R. W.; Sa-Ei, K. Tetrahedron 2002, 58, 5957.
10. Kozikowski, A. P.; Chen, Y.-Y. J. Org. Chem. 1981, 46, 5248.
11. Sakai, R.; Kamiya, H.; Murata, M.; Shimamoto, K. J. Am. Chem. Soc. 1997, 119, 4112.
12. For a review on the use of 1,3-amino alcohols in asymmetric synthesis, see: (a) Lait, S. M.; Rankic, D. A.; Keay, B. A. Chem. Rev. 2007, 107, 767.
13. (a) Barluenga, J.; Olano, B.; Fustero, S. J. Org. Chem. 1985, 50, 4052.
14. (b) Pilli, R. A.; Russowsky, D.; Dias, L. C. J. Chem. Soc. Perkin Trans. 1 1990, 1213.
15. (c) Barluenga, J.; Aguilar, E.; Fustero, S.; Olano, B.; Viado, A. J. Org. Chem. 1992, 57, 1219, and references cited therein.
16. (d) Keck, G. E.; Truong, A. P. Org. Lett. 2002, 4, 3131.
17. (a) Narasaka, K.; Ukaji, Y.; Yamazaki, S. Bull. Chem. Soc. Jpn. 1986, 59, 525.
18. (b) Williams, D. R.; Osterhout, M. H. J. Am. Chem. Soc. 1992, 114, 8750.
19. (c) Veenstra, S. J.; Kinderman, S. S. Synlett 2001, 1109.
20. Toujas, J.-L.; Toupet, L.; Vaultier, M. Tetrahedron 2000, 56, 2665.
21. For a review see: Tramontini, M. Synthesis 1982, 605.
22. Reduction of enantiopure β-amino ketones: (a) Davis, F. A.; Chao, B. Org. Lett. 2000, 2, 2623.
23. (b) Davis, F. A.; Prasad, K. R.; Nolt, B. M.; Wu, Y. Org. Lett. 2003, 5, 923.
24. (c) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
25. (d) Kennedy, A.; Nelson, A.; Perry, A. Synlett 2004, 967.
26. (e) Huguenot, F.; Brigaud, T. J. Org. Chem. 2006, 71, 2159.
27. Kochi, T.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 2002, 124, 6518.
28. Lanter, J. C.; Chen, H.; Zhang, X.; Sui, Z. Org. Lett. 2005, 7, 5905.
29. Davis, F. A.; Yang, B. Org. Lett. 2003, 5, 5011.
30. For recent reviews on the chemistry of sulfmimines, see: (a) Morton, D.; Stockman, R. A. Tetrahedron 2006, 62, 8869.
31. (b) Senanayake, C. H.; Krishnamurthy, D.; Lu, Z.-H.; Han, Z.; Gallou, I. Aldrichimica. Acta 2005, 38, 93.
32. (c) Zhou, P.; Chem, B.-C.; Davis, F. A. Tetrahedron 2004, 60, 8003.
33. (d) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984.
34. 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.
35. Davis, F. A.; Song, M. Org. Lett. 2007, 9, 2413.
36. For a review on S-N chemistry, which includes sulfinimines and sulfmimine-derived chiral building blocks, see: Davis, F. A. J. Org. Chem. 2006, 71, 8993.
37. For recent reviews on sulfinimine-derived chiral building blocks, see: (a) Davis, F. A.; Chao, B.; Andemichael, Y. W.; Mohanty, P. K.; Fang, T.; Burns, D. M.; Rao, A.; Szewczyk, J. M. Heteroatom Chem. 2002, 13, 486.
38. (b) Davis, F. A.; Yang, B.; Deng, J.; Zhang, J. ARKIVOC 2006, 120.
39. Evans, D. A.; Chapman, K. T.; Carreria, E. M. J. Am. Chem. Soc. 1988, 110, 3560.
40. Kathawala, F. G.; Prager, B.; Prasad, K.; Repic, O.; Shapiro, M. J.; Stabler, R. S.; Widler, L. Helv. Chem. Acta 1986, 69, 803.
41. Jager, V.; Buss, V. Liebgs Ann. Chem. 1980, 110.
42. Strunz, G. M.; Findlay, J. A. Pyridine and Piperidine Alkaloids, The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985; Vol. 26, p 89.
43. Schneider, M. J.; Montali, J. A.; Hazen, D.; Stanton, C. E. J. Nat. Prod. 1991, 54, 905.
44. (a) Gebauer, J.; Rost, D.; Blechen, S. Heterocycles 2006, 68, 2129.
45. (b) Fréville, S.; Delbecq, P.; Thuy, V. M.; Petit, H.; Célérier, J. P.; Lhommet, G. Tetrahedron Lett. 2001, 42, 4609.
46. (c) Molander, G. A.; Dowdy, E. D.; Pack, S. K. J. Org. Chem. 2001, 66, 4344.
47. (d) Takahata, H.; Yotsui, Y.; Momose, T. Tetrahedron 1998, 54, 13505.
48. (a) 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. Org. Chem. 1997, 62, 2555.
49. (b) Davis, F. A.; Zhang, Y.; Andemichael, Y.; Fang, T.; Fanelli, D.; Zhang, H. J. Org. Chem. 1999, 64, 1403.
50. Davis, F. A.; Zhang, H.; Lee, S. H. Org. Lett. 2001, 3, 759.
51. Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. J. Am. Chem. Soc. 1999, 64, 1278.
52. Zhao, C.-H.; Liu, Li.; Wang, D.; Chen, Y.-J. Eur. J. Org. Chem. 2006, 2977.