Enantiodivergent synthesis of D- and L-erythro-sphingosines through Mannich-type reactions of N-benzyl-2,3-O-isopropylidene-D-glyceraldehyde nitrone

Journal of Organic Chemistry

Volumn 71, Issue 12, 2006, Pages 4685-4688

  Merino, Pedro ^a   Jimenez, Pablo ^a   Tejero, Tomas ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2-SILYLOXY SILYLKETENE; ENANTIODIVERGENT SYNTHESIS; ENANTIOMERS;

ALDEHYDES; REACTION KINETICS; SYNTHESIS (CHEMICAL); ZINC COMPOUNDS;

AROMATIC COMPOUNDS;

BETA AMINO ACID; GLYCERALDEHYDE; HYDRAZONE DERIVATIVE; HYDROXYLAMINE; IMINE; KETENE DERIVATIVE; LEWIS ACID; N BENZYL 2,3 O ISOPROPYLIDINE DEXTRO GLYCERALDEHYDE NITRONE; NITRONE; SPHINGOSINE DERIVATIVE; TIN CHLORIDE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG; ZINC;

ADDITION REACTION; ARTICLE; ASYMMETRIC SYNTHESIS; CHEMICAL STRUCTURE; DESILYLATION; DIASTEREOISOMER; MANNICH REACTION; REACTION ANALYSIS; REPRODUCIBILITY; WITTIG REACTION;

NITROGEN OXIDES; SPHINGOSINE; STEREOISOMERISM;

EID: 33744932158     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060465t     Document Type: Article

References (55)

1. (a) Córdova, A. Acc. Chem. Res. 2004, 37, 102-112.
2. (b) Arend, M.; Westermann, B.; Rich, N. Angew. Chem., Int. Ed. 1998, 37, 1045-1070.
3. (c) Kleinman, E. F. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford. 1991; Vol. 2, pp 893-951.
4. (d) Arend, M.; Wang, X.; Wirth, T. In Organic Synthesis Highlights V.; Schmalz, H.-G., Ed.; Wiley-VCH Verlag: Weinheim, Germany, 2003; pp 134-143.
5. (e) Liu, M.; Sibi, M. P. Tetrahedron 2002, 58, 7991-8035.
6. (f) Burk, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3221-3242.
7. For some recent and representative examples, see: (a) Akiyama, T.; Suzuki, A.; Fuchibe, K. Synlett 2005, 1024-1026.
8. (b) Jaber, N.; Assie, M.; Fiaud, J.-C.; Collin, J. Tetrahedron 2004, 60, 3075-3084.
9. (c) Bari, L. D.; Guillarme, S.; Hermitage, S.; Howard, J. A.; Jay, D. A.; Pescitelli, G.; Whiting, A.; Yufit, D. S. Synlett 2004, 708-710.
10. (d) Jacobsen, M. F.; Skrydstrup, T. J. Org. Chem. 2003, 68, 7112-7114.
11. (e) Saaby, S.; Nakama, K.; Lie, M. A.; Hazel, R. G.; Jorgensen, K. A. Chem.-Eur. J. 2003, 9, 6145-6154.
12. (f) Ishimaru, K.; Kojima, T. J. Org. Chem. 2003, 68, 4959-4962.
13. (g) Kobayashi, S.; Matsubara, R.; Nakamura, Y.; Kitagawa, H.; Sugiura, M. J. Am. Chem. Soc. 2003, 125, 2507-2515.
14. (h) Nagano, Y.; Orita, A.; Otera, J. Tetrahedron 2003, 59, 5569-5578.
15. (i) Ueno, M.; Ishitani, H.; Kobayashi, S. Org. Lett. 2002, 4, 3395-3397.
16. (j) Wenzel, A. G.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 12964-12965.
17. (k) Kobayashi, S.; Kobayashi, J.; Ishiani, H.; Ueno, M. Chem.-Eur. J. 2002, 8, 4185-4190.
18. (a) Okino, T.; Hoashi, Y.; Takemoto, Y. Tetrahedron Lett. 2003, 44, 2817-2820.
19. (b) Murahashi, S.-I.; Imada, Y.; Kawakami, T.; Harada, K.; Yonemushi, Y.; Tomita, N. J. Am. Chem. Soc. 2002, 124, 2888-2889.
20. (c) Qian, C.; Wang, L. Tetrahedron 2000, 56, 7193-7197.
21. (d) Kawakami, T.; Ohtake, H.; Arakawa, H.; Okachi, T.; Imada, Y.; Murahashi, S.-I. Bull. Chem. Soc. Jpn. 2000, 73, 2423-2444.
22. (e) Ohtake, H.; Imada, Y.; Murahashi, S.-I. J. Org. Chem. 1999, 64, 3790-3791.
23. (f) Jost, S.; Gimbert, Y.; Greene, A. E. J. Org. Chem. 1997, 62, 6672-6677.
24. (g) DeGiorgis, F.; Lombardo, M.; Trombini, C. Synthesis 1987, 1243-1245.
25. (h) Kita, Y.; Tamura, O.; Itoh, F.; Kishino, N.; Miki, T.; Kohno, M.; Tamura, Y. Chem. Pharm. Bull. 1989, 37, 2002-2007.
26. (a) Diez, E.; Prieto, A.; Simon, M.; Vazquez, J.; Alvarez, E.; Fernandez, R.; Lassaletta, J. M. Synthesis 2006, 540-550.
27. (b) Jacobsen, M. F.; Ionita, L.; Skrydstrup T. J. Org. Chem. 2004, 69, 4792-4796.
28. (c) El-Kaim, L.; Grimaud, L.; Perroux, Y.; Tirla, C. J. Org. Chem. 2003, 68, 8733-8735.
29. (d) Allan, V.; Bienayme, H.; El-Kaim, L.; Majee, A. Chem. Commun. 2000, 1585-1586.
30. (e) Manabe, K.; Oyamada, H.; Sugita, K.; Kobayashi, S. J. Org. Chem. 1999, 64, 8054-8057.
31. (a) Ullah, E.; Rotzoll, S.; Schmidt, A.; Michalik, D.; Langer, P. Tetrahedron Lett. 2005, 46, 8997-8999.
32. (a) Ha, H.-J.; Ahn, Y.-G.; Lee, G. S. Tetrahedron: Asymmetry 1999, 10, 2327-2336.
33. (b) Ha, H. J.; Choi, C. J.; Lee, W. K. Svnth. Commun. 2002, 32, 1495-1500.
34. (c) Saito, S.; Uedo, E.; Kato, Y.; Murakami, Y.; Ishikawa, T. Synlett 1996, 1103-1104.
35. Merino, P.; Alamo, E. M.; Bona, M.; Franco, S.; Merchan, F. L.; Tejero, T.; Vieceli, O. Tetrahedron Lett. 2000, 41, 9239-9243.
36. For an account, see: Merino, P.; Franco, S.; Merchan, F. L. Synlett 2000, 442-454.
37. For other recent approaches to erythro-sphingosines, see: (a) Masuda, Y.; Mori, K. Eur. J. Org. Chem. 2005, 4789-4800.
38. (b) Lim, H.-S.; Park, J.-J.; Kwangseok, K.; Lee, M.-H.; Chung, S.-K. Bioorg. Med. Chem. Lett. 2004, 14, 2499-2503.
39. (c) Raghavan, S.; Rajender, A. J. Org. Chem. 2003, 68, 7094-7097.
40. (d) Lim, H.-S.; Oh, Y.-S.; Suh, P.-G.; Chung, S.-K. Bioorg. Med. Chem. Lett. 2003, 13, 237-240.
41. (e) Lee, J.-M.; Lim, H.-S.; Chung, S.-K. Tetrahedron: Asymmetry 2002, 13, 343-347.
42. (f) Murakami, T.; Furusawa, K. Tetrahedron 2002, 58, 9257-9263.
43. (g) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092.
44. (h) Duffin, G. R.; Ellames, G. J.; Hartmann, S.; Herbert, J.; Smith, D. I. J. Chem. Soc., Perkin Trans. 1 2000, 2237-2242.
45. Merino, P.; Franco, S.; Merchan, F. L.; Tejero, T. Tetrahedron: Asymmetry 1997, 8, 3489-3496.
46. (a) Hamura, T.; Yamaguchi, H.; Kuriyama, Y.; Tanabe, M.; Miyamoto, M.; Yasui, Y.; Matsumoto, T.; Suzuki, K. Helv. Chim. Acta 2002, 85, 3589-3604.
47. (b) Hattori, K.; Yamamoto, H. Tetrahedron 1994, 50, 3099-3112.
48. (c) Hattori, K.; Yamamoto, H. J. Org. Chem. 1993, 58, 5301-5303.
49. Merino, P.; Mates, J. A. ARKIVOC 2001, part xi, BT181-D.
50. Recent studies based on NMR data of the corresponding complexes have demonstrated that nitrones act as monodentate ligands with Lewis acids: Merino, P.; Tejero, T. Unpublished results. See also ref 7.
51. For examples of the equivalence between the dioxolane ring and the hydroxymethyl group, see: Chiacchio, U.; Borrello, L.; Iannazzo, D.; Merino, P.; Piperno, A.; Rescifina, A.; Richichi, B.; Romeo, G. Tetrahedron: Asymmetry 2003, 14, 2419-2425 and references therein.
52. Yin, J.; Liu, H.; Pidgeon, C. Bioorg. Med. Chem. Lett. 1998, 8, 179-182.
53. (a) Tsunoda, H.; Ogawa, S. Liebigs Ann. Chem. 1995, 267-277.
54. (b) Shibuya, M.; Kurosu, M.; Minagawa, K.; Katayama, S.; Kitagawa, I. Chem. Pharm. Bull. 1993, 41, 1534-1544.
55. Chiacchio, U.; Rescifina, A.; Saita, M. G.; Iannazzo, D.; Romeo, G.; Mates, J. A.; Tejero, T.; Merino, P. J. Org. Chem. 2005, 70, 8991-9001.