Electrochemical deallylation of α-allyl cyclic amines and synthesis of optically active quaternary cyclic amino acids

Chemistry - A European Journal

Volumn 16, Issue 13, 2010, Pages 3970-3982

  Kirira, Peter G ^a   Kuriyama, Masami ^a   Onomura, Osamu ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

Alkylation; Allylation; Amino acids; Diastereoselectivity; Electrochemical oxidation

Indexed keywords

ALLYLATION; ALLYLATIONS; AMINO ACID ESTERS; CYCLIC AMINES; CYCLIC AMINO ACIDS; DEALLYLATION; DIASTEREO-SELECTIVITY; GRAPHITE ANODE; OPTICALLY ACTIVE; PROTECTING GROUP;

ALKYLATION; AMINATION; AMINES; AMINO ACIDS; ELECTROCHEMICAL CELLS; ESTERS; HYDROCARBONS; ORGANIC ACIDS; STEREOSELECTIVITY;

ELECTROCHEMICAL OXIDATION;

AMINO ACID; GRAPHITE; PLATINUM;

ALKYLATION; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTROCHEMISTRY; ELECTRODE; OXIDATION REDUCTION REACTION; STEREOISOMERISM;

ALKYLATION; AMINO ACIDS; ELECTROCHEMISTRY; ELECTRODES; GRAPHITE; MODELS, MOLECULAR; OXIDATION-REDUCTION; PLATINUM; STEREOISOMERISM;

EID: 77950217702     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200903512     Document Type: Article

References (72)

1. a) T. Iwasaki, H. Horikawa, K. Matsumoto, M. Miyoshi, J. Org. Chem. 1979, 44, 1552-1554;
2. b) T. Shono, Y. Matsumura, O. Onomura, M. Sato, J. Org. Chem. 1988, 53, 4118-4121;
3. c) A. Zietlow, E. Steckhan, J. Org. Chem. 1994, 59, 5658-5661;
4. d) Y. Matsumura, Y. Shirakawa, Y. Satoh, M. Umino, T. Tanaka, T. Maki, O. Onomura, Org. Lett. 2000, 2, 1689-1691;
5. e) G. Ng'ang'a Wanyoike, O. Onomura, T. Maki, Y. Matsumura, Org. Lett. 2002, 4, 1875-1877;
6. f) G. N. Wanyoike, Y. Matsumura, O. Onomura, Heterocycles 2009, 79, 339-345.
7. a) O. Loures, M. Gertjan, P. J. T. Floris, W. N. Speckamp, H. Hiemstra, Org. Lett. 1999, 1, 1331-1334; representative reviews:
8. b) M. D. Groaning, A. I. Meyers, Tetrahedron 2000, 56, 9843-9873;
9. c) P. M. Weintraub, J. S. Sabol, J. M. Kane, D. R. Borcherding, Tetrahedron 2003, 59, 2953-2989.
10. Representative reviews: a) W. N. Speckamp, M. J. Moolenaar, Tetrahedron 2000, 56, 3817-3856;
11. b) A. Yazici, S. G. Pyne, Synthesis 2009, 339-368;
12. c) A. Yazici, S. G. Pyne, Synthesis 2009, 513-541;
13. representative literatures: T. Shono, Y. Matsumura, K. Tsubata, J. Am. Chem. Soc. 1981, 103, 1172-1176;
14. d) T. Shono, Y. Matsumura, T. Kanazawa, Tetrahedron Lett. 1983, 24, 4577-4580;
15. e) T. Shono, Y. Matsumura, K. Uchida, T. Tagami, Chem. Lett. 1987, 912-922;
16. f) Y. Matsumura, J. Terauchi, T. Yamamoto, T. Konno, T. Shono, Tetrahedron 1993, 49, 8503-8512;
17. g) N. Yamazaki, T. Eto, C. Kibayashi, Synlett 1999, 37-40.
18. a) Y. Matsumura, Y. Kanda, K. Shirai, O. Onomura, T. Maki, Org. Lett. 1999, 1, 175-178;
19. b)Y. Matsumura, Y. Kanda, K. Shirai, O. Onomura, T. Maki, Tetrahedron 2000, 56, 7411-7422.
20. M. Sugiura, S. Kobayashi, Org. Lett 2001, 3, 477-480.
21. K. Koumaglo, T. H. Chan, Tetrahedron Lett. 1984, 25, 717-720.
22. J. Yoshida, S. Suga, Chem. Eur. J. 2002, 8, 2650-2658.
23. Lead(IV) acetate mediated oxidative C-C bond cleavage of N-acylα-amino acid 1 proceeded, albeit with low yields and a longer reaction, time, see : Y. Matsumura, G. N. Wanyoike, O. Onomura, T. Maki, Electrochim. Acta 2003, 48, 2957-2966.
24. I. Barba, M. Tornero, Tetrahedron 1992, 48, 9967-9977.
25. a) B. W. Metcalf, P. Bey, C. Danzin, M. J. Jung, P. Casara, J. P. Vevert, J. Am. Chem. Soc. 1978, 100, 2551-2553;
26. b) M. J. Jung, Chemistry and Biochemistry of the Amino Acids (Ed.: B. G. C. Barrett), Chapman and Hall, London, 1985, pp. 227-245.
27. Recent representative reviews: a) C. Cativiela, M. D. Díaz-de-Villegas, Tetrahedron: Asymmetry 2007, 18, 569-623;
28. b) M. I. Calaza, C. Cativiela, Eur. J. Org. Chem. 2008, 3427-3448;
29. c) C. Cativiela, M. Ordonez, Tetrahedron: Asymmetry 2009, 20, 1-63;
30. recent representative literature: d)T. Kawabata, K. Moriyama, S. Kawakami, K. Tsubaki, J. Am. Chem. Soc. 2008, 130, 4153-4157;
31. e) S. Cabrera, E. Reyes, J. Aleman, A. Milelli, S. Kobbelgaard, K. A. Jørgensen, J. Am. Chem. Soc. 2008, 130, 12031-12037;
32. f)M. Kitamura, S. Shirakawa, Y. Arimura, X. Wang, K. Maruoka, Chem. Asian J. 2008, 3, 1702-1714;
33. g) M. Terada, H. Tanaka, K. Sorimachi, J. Am. Chem. Soc. 2009, 131, 3430-3431;
34. h) F. R. Bou-Hamdan, J. L. Leighton, Angew. Chem. 2009, 121, 2439-2442;
35. Angew. Chem. Int. Ed. 2009, 48, 2403-2406;
36. i) M. Branca, S. Pena, R. Guillot, D. Gori, V. Alezra, C. Kouklovsky, J. Am. Chem. Soc. 2009, 131, 10711-10718;
37. j) V. Lupi, M. Penso, F. Foschi, F. Gassa, V. Mihali, A. Tagliabue, Chem. Commun. 2009, 5012-5014;
38. k) P. Tuzina, P. Somfai, Org. Lett. 2009, 11, 919-921.
39. a) T. Shono, Y. Matsumura, K. Tsubata, K. Uchida, J. Org. Chem. 1.986, 51, 2590-2592;
40. b) Y. Demizu, H. Shiigi, H. Mori, K. Matsumoto, O. Onomura, Tetrahedron: Asymmetry 2008, 19, 2659-2665.
41. Recently, Kawabata and co-workers prepared quaternary cyclic amino acid derivatives by starting from acyclic N-ω-bromoalkyl-Nfert-butoxycarbonyl- a-amino acid derivatives in up to 99% ee, see: reference [11d].
42. J. Bajgrowicz, A. El Achquar, M. Roumestant, C. Pigiere, P. Viallefont, Heterocycles 1986, 24, 2165-2167.
43. J. Muzart, Tetrahedron 2009, 65, 8313-8323.
44. 4-mediated α-allylation of methyl α-methoxy-N-methoxycarbonyl-L-prolinate with allyl-TMS proceeded with moderate diastereoselectivity (46% de): O. Onomura, P. G. Kirira, T. Tanaka, S. Tsukada, Y. Matsumura, Y. Demizu, Tetrahedron 2008, 64, 7498-7503.
45. Prepared in 34% yield according to A. D. Dilman, D. E. Arkhipov, A. A. Korlyukov, V. P. Ananikov, V. M. Danilenko, V. A. Tartakovsky, J. Organomet. Chem. 2005, 690, 3680-3689.
46. 20=-30.0 (c=1.0 in EtOH)];
47. b) Sandoz Ltd, Netherland Patent No. 6609202, 1967;
48. [Chem. Abstr. 1967, 82297];
49. c) the absolute configuration of 35 was deduced on the basis of retention of configuration as observed in compound 34.
50. For some selected literature on 1,3-asyrnmetric induction, see: a) Y. F. Wang, T. Izawa, S. Kobayashi, M. Ohno, J. Am. Chem. Soc. 1982, 104, 6465-6466;
51. b) M. T. Reetz, A. Jung, J. Am. Chem. Soc. 1983, 105, 4833-4835;
52. c) G. A. Molander, J. B. Etter, L. S. Hairing, P. J. Thorel, J. Am. Chem. Soc. 1991, 113, 8036-8045;
53. d) D. A. Evans, M. J. Dart, J. L. Duffy, M. G. Yang, J. Am. Chem. Soc. 1996, 118, 4322-4343;
54. e)B. Bret, Eur. J. Org. Chem. 1998, 1123-1134;
55. f) R. Lazzaroni, S. Rocchiccioli, A. Luliano, L. Cipolla, F. Nicotra, Tetrahedron: Asymmetry 2005, /6, 3661-3666.
56. Compounds 4a-j were prepared by electrochemical oxidation from their respective N-acyl cyclic amines; for 4a,b: a) T. Shono, H. Hamaguchi, Y. Matsumura, J. Am. Chem. Soc. 1975, 97, 4264-4268;
57. for 4c: reference [4]; for 4d: see the Experimental Section;
58. b) for 4e-g: T. Shono, Y. Matsumura, T. Kanazawa, M. Habuka, K. Uchida, K. Toyoda, J. Chem. Res 1984, 2873-2889;
59. for 4h: see the Experimental Section; for 4i:
60. c) T. Shono, Y. Matsumura, T. Kanazawa, Tetrahedron Lett. 1983, 24, 1259-1262; for 4j:
61. d) T. Nishitani, H. Horilawa, T. Iwasaki, K. Matsumoto, I. Inoue, M. Mlyoshi, J. Org. Chem. 1982, 47, 1706-1712; for 4k:
62. e) T. Nagasaka, H. Tamano, F. Hamaguchi, Heterocycles 1986, 24, 1231-1232.
63. J. Yoshida, S. Suga, S. Suzuki, N. Kinomura, A. Yamamoto, K. Fujiwara, J. Am. Chem. Soc. 1999, 121, 9546-9549.
64. T. Shono, Y. Matsumura, O. Onomura, M. Ogaki, T. Kanazawa, J. Org. Chem. 1987, 52, 536-541.
65. S. Young-Ger, K. Seok-Ho, J. Jae-Kyung, S. Dong-Yun, Tetrahedron Lett. 2002, 45, 3165-3168.
66. M.-J. Tranchant, C. Moine, R. B. Othman, T. Bousquet, M. Othman, V. Dalla, Tetrahedron Lett. 2006, 47, 4477-4480.
67. S. S. Libendi, Y. Demizu, Y. Matsumura, O. Onomura, Tetrahedron 2008, 64, 3935-3942.
68. A. Boto, D. Hernandez, R. Hernandez, A. Montoya, E. Suarez, Eur. J. Org. Chem. 2007, 325-334.
69. T. Shono, J. Terauchi, K. Kitayarna, Y. Takeshima, Y. Matsumura, Tetrahedron 1992, 48, 8253-8262.
70. D. Minato, Y. Nagasue, Y. Demizu, O. Onomura, Angew. Chem. 2008, 120, 9600-9603;
71. Angew. Chem. Int. Ed. 2008, 47, 9458-9461.
72. Y. Matsumura, T. Kinoshita, Y. Yanagihara, N. Kanemoto, M. Wata- nabe, Tetrahedron Lett. 1996, 37, 8395-8398.