Stereoselective synthesis of syn- and anti-1,2-aminoalcohols using iridium-catalyzed allylic amination reactions

Synlett

Volumn , Issue 14, 2009, Pages 2281-2286

  Ichikawa, Yoshiyasu ^a   Yamamoto, Shun Ichi ^a   Kotsuki, Hiyoshizo ^a   Nakano, Keiji ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

Allylic amination; Amino alcohol; Catalysis; Iridium; Transition metals

Indexed keywords

1,2 AMINOALCOHOL DERIVATIVE; 1,2 DIHYDROXYINDOLIZINE; ALLYL COMPOUND; AMINO ACID; AMINOALCOHOL; FUMARIC ACID DIMETHYL ESTER; INDOLIZINE DERIVATIVE; IRIDIUM; OXAMIC ACID; POLYOXAMIC ACID; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 69449086274     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217814     Document Type: Article

References (55)

1. (a) Ager, D. J.; Prakash, I.; Scheed, D. R. Chem. Rev. 1996, 96, 835.
2. (b) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
3. For isolation, see: (a) Isono, K.; Asahi, K.; Suzuki, S. J. Am. Chem. Soc. 1969, 91, 7499.
4. For synthetic works, see: (b) Saksena, A. K.; Lovey, R. G.; Girijavallabhan, V. M.; Ganguly, A. K. J. Org. Chem. 1986, 51, 5024.
5. (c) Hirama, M.; Hioki, H.; Ito, S. Tetrahedron Lett. 1988, 29, 3125.
6. (d) Garner, P.; Park, J. M. J. Org. Chem. 1988, 53, 2979.
7. (e) Dureult, A.; Carreaux, F.; Depezay, J.-C. Tetrahedron Lett. 1989, 30, 4527.
8. (f) Paz, M.; Sardina, F. J. Org. Chem. 1993, 58, 6990.
9. (g) Dondoni, A.; Franco, S.; Merchan, F. L.; Merino, P.; Tejero, T. Tetrahedron Lett. 1993, 34, 5479.
10. (h) Marshall, J. A.; Seletsky, B. M.; Coan, P. S. J. Org. Chem. 1994, 59, 5139.
11. (i) Matsura, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1994, 35, 733.
12. (j) Jackson, R. F.; Palmer, N. J.; Wyther, M. J.; Clegg, W.; Elsegood, M. J. Org. Chem. 1995, 60, 6431.
13. (k) Kang, S. H.; Choi, H. Chem. Commun. 1996, 1521.
14. (l) Veeresa, G.; Datta, A. Tetrahedron Lett. 1998, 39, 119.
15. (m) Savage, I.; Thomas, E. J.; Wilson, P. D. J. Chem. Soc., Perkin Trans. 1 1999, 3291.
16. (n) Davis, F. A.; Prasad, K. R.; Carroll, P. J. J. Org. Chem. 2002, 67, 7802.
17. (o) Tarrade, A.; Dauban, P.; Dodd, R. H. J. Org. Chem. 2002, 68, 9521.
18. (a) Harris, T. M.; Harris, C. M. H.; Hill, J. E.; Ungemach, F. S.; Broquist, H. P.; Wickwire, B. M. J. Org. Chem. 1987, 52, 3094.
19. (b) Heitz, M.-P.; Overman, L. E. J. Org. Chem. 1989, 54, 2591.
20. (a) Ichikawa, Y.; Ito, T.; Isobe, M. Chem. Eur. J. 2005, 11, 1949.
21. (b) Ichikawa, Y.; Matsunaga, K.; Masuda, T.; Kotsuki, H.; Nakano, K. Tetrahedron 2008, 64, 11313.
22. (a) Takeuchi, R.; Ue, N.; Tanabe, K.; Yamashita, K.; Shiga, N. J. Am. Chem. Soc. 2001, 123, 9525.
23. For the allylic alkylation, see: (b) Takeuchi, R.; Kashio, M. Angew. Chem. Int. Ed. Engl. 1997, 36, 263.
24. (c) Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647.
25. For reviews, see: (d) Takeuchi, R. Synlett 2002, 1954.
26. (e) Takeuchi, R.; Kezuka, S. Synthesis 2006, 3349.
27. Ohmura, T.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 15164.
28. (a) Feringa, B. L. Acc. Chem. Res. 2000, 346.
29. For a convenient synthetic method for L1 and L2 ligands, see: (b) Alexakis, A.; Gille, S.; Prian, F.; Rosset, S.; Ditrich, K. Tetrahedron Lett. 2004, 45, 1449.
30. (c) Polet, D.; Alexakis, A. Org. Lett. 2005, 7, 1621.
31. (a) Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 116.
32. (b) Welter, C.; Koch, O.; Lipowsky, G.; Helmchen, G. Chem. Commun. 2004, 896.
33. (c) Helmchen, G. Chem. Commun. 2004, 116.
34. (d) Weihofen, R.; Dahnz, A.; Tverskoy, O.; Helmchen, G. Chem. Commun. 2005, 3541.
35. (e) Weihofen, R.; Tverskoy, O.; Helmchen, G. Angew. Chem. Int. Ed. 2006, 45, 5546.
36. (f) Lee, J. H.; Shin, S.; Kang, J.; Lee, S. J. Org. Chem. 2007, 72, 7443.
37. Ichikawa, Y.; Tsuboi, K.; Isobe, M. J. Chem. Soc., Perkin Trans. 1 1994, 2791.
38. Hartwig reported that solvent influences the reactivity and enantioselectivity of enantioselective allylic amination. Although reactions in the polar solvents, such as DMF and EtOH were fast (100% conversion after 2 h), low ee's were observed (80-77% ee). As a result, THF was recommended as the most suitable balance of rate (100% conversion after 8-10 h) and enantioselectivity (95% ee). See reference 6.
39. (a) Kiener, C. A.; Shu, C.; Incarvito, C.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 14272.
40. (b) Leitner, A.; Shu, C.; Hartwig, J. F. Org. Lett. 2005, 7, 1093.
41. Shu, C.; Leitner, A.; Hartwig, J. F. Angew. Chem. Int. Ed. 2004, 43, 4797.
42. (a) Fukuyama, T.; Frank, R. K.; Jewell, C. F. J. Am. Chem. Soc. 1980, 102, 2122.
43. (b) Kronenthal, D. R.; Han, C. Y.; Taylor, M. K. J. Org. Chem. 1982, 47, 2765.
44. 3, 100 MHz): δ = -5.08, -4.16, 18.0, 20.6, 25.7, 55.3, 55.7, 62.5, 70.6, 99.1, 103.6, 111.8, 117.4, 131.5, 136.3, 148.3, 151.7.
45. The allylic amination of 6 with an achiral iridium complex decorated with triphenylphosphite was briefly investigated. In this case, a 53:47 mixture of products 10b and 11b, together with recovered starting material 6 (17%) was isolated (77% yield based on the consumed starting material; Scheme 7). (Chemical Equation Presented)
46. Our initial attempts to promote N-dearylation of 11a with CAN were complicated by formation of varying amounts of p-quinone ii (Scheme 8). See also the reference 18b. (Chemical Equation Presented)
47. A competitive experiment using a 1:1 mixture of p-anisidine and 2,4-dimethoxyaniline was carried out in order to compare reactivity. In this reaction, a 7:3 mixture of products 10b and 10a was obtained in 86% combined yield (Scheme 9). This indicates that 2,4-dimethoxyaniline is approximately two times more nucleophilic than p-anisidine. (Chemical Equation Presented)
48. For the empirical rule for assignment of relative configurations of trans- and cis-oxazolidinones, see: (a) Futagawa, S.; Inui, T.; Shiba, T. Bull. Chem. Soc. Jpn. 1973, 46, 3308.
49. 1,2 values between 15 (7.2 Hz) and 16 (7.7 Hz) may not allow the use of empirical rule reported by Futagawa.
50. C = 19.6 ppm for i and 16.8 ppm for ii) may support the assignment of relative stereochemistry (Figure 4). (Chemical Equation Presented)
51. 3, 100 MHz): δ = -4.90, -4.48, 17.9, 20.7, 25.7, 52.0, 58.6, 70.0, 115.2, 137.2, 156.8.
52. In initial attempts to synthesize the intermediate in the polyoxamic acid synthesis, allylic carbonate i was synthesized from an intermediate prepared in our previous synthesis of polyoxamic acid (ref. 4a). Iridium-catalyzed allylic amination of i resulted in predominant formation of the linear product ii, and none of desired branched products was recognized (Scheme 10). It appears that the acetonide group is responsible for the erosion in regioselectivity through steric interactions and/or chelation effects. Further studies to reveal the effects of protecting groups on the iridium-catalyzed allylic amination reaction are underway. (Chemical Equation Presented)
53. Wei, C. C.; Bernardo, S. D.; Tengi, J. P.; Borgese, J.; Weigele, M. J. Org. Chem. 1985, 50, 3462.
54. (a) Cohen, N.; Banner, B. L.; Laurenzano, A. J.; Carozza, L. Org. Synth. Coll. Vol.7; John Wiley & Sons: London, 1990, 297.
55. (b) Hinman, A.; Du Bois, J. J. Am. Chem. Soc. 2003, 125, 11510.