A regio- and stereodivergent route to all isomers of vic-amino alcohols

Journal of Organic Chemistry

Volumn 67, Issue 24, 2002, Pages 8574-8583

  Olofsson, Berit ^a   Somfai, Peter ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOPHILES;

ALCOHOLS; SYNTHESIS (CHEMICAL);

ISOMERS;

ALLYL COMPOUND; AMINOALCOHOL; EPOXIDE; LIGAND; NATURAL PRODUCT; UNCLASSIFIED DRUG; VINYL DERIVATIVE; VINYLAZIRIDINE DERIVATIVE;

AMINOLYSIS; ARTICLE; ENANTIOMER; ENANTIOSELECTIVITY; ISOMER; LYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS; CATALYSIS; CHEMISTRY; COMBINATORIAL CHEMISTRY; HYDROLYSIS;

AMINO ALCOHOLS; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROLYSIS; STEREOISOMERISM; VINYL COMPOUNDS;

EID: 0037195680     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0262053     Document Type: Article

References (74)

1. Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431-432.
2. Castejon, P.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron 1996, 52, 7063.
3. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
4. Reetz, M. T. Angew. Chem., Int. Ed. Engl. 1991, 30, 1531-1546.
5. (a) Enders, D.; Haertwig, A.; Raabe, G.; Runsink, J. Eur. J. Org. Chem. 1998, 1771-1792.
6. (b) Enders, D.; Haertwig, A.; Runsink, J. Eur. J. Org. Chem. 1998, 1793-1802.
7. Hattori, K.; Yamamoto, H. Tetrahedron 1994, 50, 2785-2792.
8. Barrett, A. G. M.; Seefeld, M. A.; White, A. J. P. J. Org. Chem. 1996, 61, 2677-2685.
9. (a) Li, G.; Chang, H.-T.; Sharpless, B. K. Angew. Chem., Int. Ed. Engl. 1996, 35, 451.
10. (b) O'Brien, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 326-329.
11. (a) Hayakawa, H.; Okada, N. M. M.; Miyashita, M. Tetrahedron Lett. 1999, 40, 4589-4592.
12. (b) Larrow, J. F.; Schaus, S. E.; Jacobsen, E. N. J. Am. Chem. Soc. 1996, 118, 7420-7421.
13. (c) Mitsunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 6, p Chapter 1.3.
14. (d) Zwanenburg, B. Pure Appl. Chem. 1999, 71, 423-430.
15. Takeuchi, H.; Koyama, K. J. Chem. Soc., Perkin Trans. 2 1981, 121-126.
16. (a) Ibuka, T.; Nakai, K.; Akaji, M.; Tamamura, H.; Fujii, N.; Yamamoto, Y. Tetrahedron 1996, 52, 11739-11752.
17. (b) Cantrill, A. A.; Osborn, H. M. I.; Sweeney, J. Tetrahedron 1998, 54, 2181-2208.
18. (c) Hwang, G.-I.; Chung, J.-H.; Lee, W. K. J. Org. Chem. 1996, 61, 6183-6188.
19. (a) Lohray, B. B.; Gao, Y.; Sharpless, K. B. Tetrahedron Lett. 1989, 30, 2623-2626.
20. (b) Lohray, B. B.; Ahuja, J. R. J. Chem. Soc., Chem. Commun. 1991, 95-97.
21. (a) Chang, H.-T.; Sharpless, B. Tetrahedron Lett. 1996, 37, 3219-3222.
22. (b) Cho, G. Y.; Ko, S. Y. J. Org. Chem. 1999, 64, 8745-8747.
23. Olofsson, B.; Khamrai, U.; Somfai, P. Org. Lett. 2000, 2, 4087-4089.
24. Frohn, M.; Dalkiewicz, M.; Tu, Y.; Wang, Z.-X.; Shi, Y. J. Org. Chem. 1998, 63, 2948-2953.
25. Jaime, C.; Ortuno, R., M.; Font, J. J. Org. Chem. 1988, 53, 139-141.
26. Díez-Martin, D.; Kotecha, N. R.; Ley, S. L.; Mantegani, S.; Menéndez, J. C.; Organ, H. M.; White, A. D.; Banks, J. B. Tetrahedron 1992, 48, 7899-7938.
27. See Supporting Information.
28. Weigand, S.; Bruckner, R. Synlett 1997, 225-228.
29. Lindström, U. M.; Somfai, P. Chem. Eur. J. 2001, 7, 94-98.
30. Analyzed by HPLC using ChiralCel OJ or ChiralCel OD-H.
31. Bergmeier, S. C. Tetrahedron 2000, 56, 2561-2576.
32. Lindström, U. M.; Somfai, P. Synthesis 1998, 109-117.
33. Lindström, U. M.; Franckowiak, R.; Pinault, N.; Somfai, P. Tetrahedron Lett. 1997, 38, 2027-2030.
34. Lindström, U. M.; Olofsson, B.; Somfai, P. Tetrahedron Lett. 1999, 40, 9273-9276.
35. Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
36. 1H NMR.
37. (a) Sekar, G.; Singh, V. K. J. Org. Chem. 1999, 64, 287-289.
38. (b) Cristau, H.-J.; Pirat, J.-L.; Drag, M.; Kafarski, P. Tetrahedron Lett. 2000, 41, 9781-9785.
39. Perreux, L.; Loupy, A. Tetrahedron 2001, 57, 9199-9223.
40. 4OH at 50 W for 8 min.
41. (a) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1988, 110, 7933-7935.
42. (b) Trost, B. M.; Sudhakar, A. R. J. Am. Chem. Soc. 1987, 109, 3792-3794.
43. Cook, G. R.; Shanker, S. Tetrahedron Lett. 1998, 39, 3405-3408.
44. The temperature was decreased from room temperature to 0 °C; further decrease caused formation of a new byproduct.
45. Heathcock, C. H.; Blumenkopf, T. A.; Smith, K. M. J. Org. Chem. 1989, 54, 1548-1562.
46. (a) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II, A Review of the Literature 1982-1995; Padwa, A., Ed.; Pergamon: Elmsford, NY, 1996; Vol. 1A, pp 1-96.
47. (b) Tanner, D. Angew. Chem., Int. Ed. Engl. 1994, 33, 599-619.
48. (c) Hughes, D. L. Org. Prep. Proc. Int. 1996, 28, 127-164.
49. (d) Osborn, H. M. I.; Sweeney, J. Tetrahedron: Asymmetry 1997, 8, 1693-1715.
50. Olofsson, B.; Wijtmans, R.; Somfai, P. Tetrahedron 2002, 58, 5979-5982.
51. Other solvent systems destroyed the silica deactivation and gave unpure aziridine.
52. (a) Viallon, L.; Reinaud, O.; Capdevielle, P.; Maumy, M. Tetrahedron 1996, 52, 13505-13614.
53. (b) Wipf, P.; Henninger, T. C.; Geib, S. J. J. Org. Chem. 1998, 63, 6088-6089.
54. Optimization attempts failed; neither prolonged reaction time nor a large excess of reagents improved the conversion; instead, a byproduct was formed.
55. Ibuka, T.; Nakai, K.; Habashita, H.; Hotta, Y.; Otaka, A.; Tamamura, H.; Fujii, N. J. Org. Chem. 1995, 60, 2044-2058.
56. Prasad, B. A. B.; Sekar, G.; Singh, V. K. Tetrahedron Lett. 2000, 41, 4677-4679.
57. (a) Parrodi, C. A.; Vazquez, V.; Quintero, L.; Juraristi, E. Synth. Commun. 2001, 31, 3295-3302.
58. (b) Yadav, J. S.; Reddy, B. V. S.; Jyothirmai, B.; Murty, M. S. R. Synlett 2002, 53-56.
59. (a) Yadav, J. S.; Reddy, B. V. S.; Abraham, S.; Sabitha, G. Tetrahedron Lett. 2002, 43, 1565-1567.
60. (b) Fringuelli, F.; Pizzo, F.; Vaccaro, L. J. Org. Chem. 2001, 66, 3554-3558.
61. Reduced temperature considerably decreased the reactivity, and with a catalytic amount of acid, the reaction proceeded only at reflux with poor selectivity (dr 1.3:1).
62. Lindström, U. M.; Somfai, P. J. Am. Chem. Soc. 1997, 119, 8385-8386.
63. Cardillo, G.; Gentilucci, L.; Tolomelli, A.; Tomasini, C. Tetrahedron Lett. 1997, 38, 6953-6956.
64. Nishiguchi, T.; Tochio, H.; Nabeya, A.; Iwakura, Y. J. Am. Chem. Soc. 1968, 91, 5835-5845.
65. Foglia, T. A.; Gregory, L. M.; Maerker, G. J. Org. Chem. 1970, 35, 3779-3785.
66. Hori, K.; Nishiguchi, T.; Nabeya, A. J. Org. Chem. 1997, 62, 3081-3088.
67. Ferraris, D.; Drury, W. J., III; Cox, C.; Lectka, T. J. Org. Chem. 1998, 63, 4568-4569.
68. (a) Lee, K.-Y.; Kim, Y.-H.; Park, M.-S.; Oh, C.-Y.; Ham, W.-H. J. Org. Chem. 1999, 64, 9450-9458.
69. (b) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd Ed.; Wiley: New York, 1999.
70. 3 cleaved both the amide and benzyl group.
71. Evans, D. A.; Ratz, A. M.; Huff, B. E.; Sheppard, G. S. J. Am. Chem. Soc. 1995, 117, 3448-3467.
72. Gosmann, G.; Guillaume, D.; Husson, H.-P. Tetrahedron Lett. 1996, 37, 4369-4372.
73. Sepulveda-Arques, J.; Armero-Alarte, T.; Acero-Alarcon, A.; Zaballos-Garcia, E.; Solesio, B. Y.; Carrera, J. E. Tetrahedron 1996, 52, 2097-2102.
74. dba = dibenzylideneacetone.