Synthesis and properties of 1-aminocyclopropane-1,2-dicarboxylic acid and compounds incorporating it

Russian Chemical Reviews

Volumn 72, Issue 4, 2003, Pages 343-355

  Krasnov, V P ^a   Korolyova, M A ^a   Levit, G L ^a  

^a INSTITUTE OF ORGANIC SYNTHESIS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748372109     PISSN: 0036021X     EISSN: 14684837     Source Type: Journal    
DOI: 10.1070/RC2003v072n04ABEH000750     Document Type: Article

References (87)

1. C H Stammer Tetrahedron 46 2231 (1990)
2. K Burgess, K-K Ho, D Moye-Sherman Synlett 575 (1994)
3. A Alami, M Calmes, J Daunis, R Jacquier Bull. Soc. Chim. Fr. 130 5 (1993)
4. T Wakamiya, H Nakamoto, T Shiba Tetrahedron Lett. 25 4411 (1984)
5. T Wakamiya, Y Oda, H Fujita, T Shiba Tetrahedron Lett. 27 2143 (1986)
6. A Ichihara, K Shiraishi, S Sakamura Tetrahedron Lett. 365 (1979)
7. S R Landor, Ph D Landor, M Kalli J. Chem. Soc., Perkin Trans. 1 2921 (1983)
8. N Kurokawa, Y Ohfune Tetrahedron Lett. 26 83 (1985)
9. K Burgess, K-K Ho, B M Pettitt J. Am. Chem. Soc. 117 54 (1995)
10. K Burgess, Ch-Y Ke J. Org. Chem. 61 8627 (1996)
11. D Lim, K Burgess J. Am. Chem. Soc. 119 9632 (1997)
12. S F Martin, R E Austin, C J Oalmann, W R Baker, S L Condon, E deLara, S H Rosenberg, K P Spina, H H Stein, J Cohen, H D Kleinert J. Med. Chem. 35 1710 (1992)
13. C Mapelli, L F Elrod, E M Holt, C H Stammer Tetrahedron 45 4377 (1989)
14. C Mapelli, L F Elrod, F L Switzer, C H Stammer Biopolymers 28 123 (1989)
15. a
16. R L Johnson, J F Koerner J. Med. Chem. 31 2057 (1988)
17. T Knōpfel, R Kuhn, H Allgeier J. Med. Chem. 38 1417 (1995)
18. K Yamanoi, Y Ohfune Tetrahedron Lett. 29 1181 (1988)
19. K Shimamoto, Y Ohfune Tetrahedron Lett. 30 3803 (1989)
20. R Pellicciari, B Natalini, M Marinozzi Tetrahedron Lett. 31 139 (1990)
21. K Shimamoto, M Ishida, H Shinozaki, Y Ohfune J. Org. Chem. 56 4167 (1991)
22. b
23. L I Deiko, K V Varlygo, in Fiziologiya i Biokhimiya Glutamatergicheskikh Sinapsov (Physiology and Biochemistry of Glutamatergic Synapses) (Ed. Yu E Mandel'shtam) (Leningrad: Nauka, 1989) p. 25
24. G A Kraus, H Kim, P J Thomas, D E Metzler, C M Metzler, J E Taylor Synth. Commun. 20 2667 (1990)
25. E C Taylor, B H Hu Synth. Commun. 26 1041 (1996)
26. S G Pyne, K Schafer, B W Skelton, A H White Aust. J. Chem. 51 127 (1998)
27. R Beumer, C Bubert, C Cabrele, O Vielhauer, M Pietzsch, O Reiser J. Org. Chem. 65 8960 (2000)
28. L A Yanovskaya, V A Dombrovskii, A Kh Khusid, in Tsiklopropany s Funktsional'nymi Gruppami (Cyclopropanes with Functional Groups) (Ed. V F Kucherov) (Moscow: Nauka, 1989) p. 106
29. J G Cannon, J E Garst J. Org. Chem. 40 182 (1975)
30. L Dechoux, E Doris Tetrahedron Lett. 35 2017 (1994)
31. R Huisgen Angew. Chem. 75 604 (1963)
32. I Bregovec, T Jakovčić Monatsh. Chem. 103 288 (1972)
33. T Hyama, M Kai Tetrahedron Lett. 23 2103 (1982)
34. J M Bland, C H Stammer, K I Varughese J. Org. Chem. 49 1634 (1984)
35. C Cativiela, M D Diaz de Villegas, E Melendez Tetrahedron 42 583 (1986)
36. J Bland, A Shah, A Bortolussi, C H Stammer J. Org. Chem. 53 992 (1988)
37. A M P Koskinen, L Muñoz J. Org. Chem. 58 879 (1993)
38. H M L Davies, P R Bruzinski, D H Lake, N Kong, M J Fall J. Am. Chem. Soc. 118 6897 (1996)
39. H Horikawa, T Nishitani, T Iwasaki, I Inoue Tetrahedron Lett. 24 2193 (1983)
40. N A Anisimova, T Ya Paperno, L I Deiko, in Sintez, Struktura i Khimicheskie Prevrashcheniya Organicheskikh Soedinenii Azota: Nitrozosoedinenii, Aminov i Aminokislot (Synthesis, Structure and Chemical Conversions of Organic Compounds of Nitrogen: Nitroso Compounds, Amines and Amino Acids) (Ed. N A Solov'ev) (Leningrad: A I Gertsen Russian State Pedagogical University, 1991) p. 97
41. c
42. c
43. c
44. b
45. WO PCT 8 500 809; Chem. Abstr. 103 215 811 (1985)
46. M Franck-Neumann, D Martina, C Dietrich-Buchecker Tetrahedron Lett. 1763 (1975)
47. M Franck-Neumann, C Buchecker Angew. Chem. 85 259 (1973)
48. b
49. S Mataka, T Ohshima, M Tashiro J. Org. Chem. 46 3960 (1981)
50. A Bojilova, I Videnova, C Ivanov, N A Rodios, A Terzis, C P Raptopoulou Tetrahedron 50 13023 (1994)
51. A Padwa, S I Goldstein Can. J. Chem. 62 2506 (1984)
52. Y Tan, S A Ahmed, H Dürr, V Huch, A Abdel-Wahab Chem. Commun. 1246 (2001)
53. T Kurihara, K Nasu, F Ishimori, T Tani J. Heterocycl. Chem. 18 163 (1981)
54. T Kurihara, K Nasu, Y Adachi J. Heterocycl. Chem. 20 81 (1983)
55. T Kurihara, K Nasu, J Byakuno, T Tani Chem. Pharm. Bull. 30 1289 (1982)
56. H Gstach, H Kisch Chem. Ber. 115 2586 (1982)
57. M Franck-Neumann, M Miesch, H Kempf Tetrahedron 44 2933 (1988)
58. G Fischer, D Hunkler, H Prinzbach, G Rihs, H Fritz Tetrahedron Lett. 25 2459 (1984)
59. K Exner, G Fischer, N Bahr, E Beckmann, M Lugan, F Yang, G Rihs, M Keller, D Hunkler, L Knothe, H Prinzbach Eur. J. Org. Chem. 763 (2000)
60. T Ueda, Y Kawabata, N Murakami, S Nagai, J Sakakibara, M Goto Chem. Pharm. Bull. 39 270 (1991)
61. A L Schwan, J Warkentin Can. J. Chem. 66 1686 (1988)
62. E Van Loock, G L'abbé, G Smets Tetrahedron 28 3061 (1972)
63. O Tsuge, M Noguchi, H Moriyama Heterocycles 19 1823 (1982)
64. L Garanti, A Vigevani, G Zecchi Tetrahedron Lett. 1527 (1976)
65. L Garanti, G Zecchi J. Heterocycl. Chem. 15 509 (1978)
66. L Garanti, G Zecchi J. Chem. Soc., Perkin Trans. 1 1195 (1979)
67. A Alemagna, P Del Buttero, E Licandro, S Maiorana Gazz. Chim. Ital. 111 285 (1981)
68. L Wick, C Tamm, T Boller Helv. Chim. Acta 78 403 (1995)
69. d
70. c
71. S Yamazaki, T Inoue, T Hamada, T Takada, K Yamamoto J. Org. Chem. 64 282 (1999)
72. S Yamazaki, M Tanaka, T Inoue, N Morimoto, H Kumagai, K Yamamoto J. Org. Chem. 60 6546 (1995)
73. S Yamazaki, M Tanaka, A Yamaguchi, S Yamabe J. Am. Chem. Soc. 116 2356 (1994)
74. X A Zhang, M M Campbell, D W Brown Chem. Res. Chin. Univ. 8 377 (1992)
75. J M Jiménez, J Rifé, R M Ortuño Tetrahedron: Asymmetry 7 537 (1996)
76. J M Jiménez, J Rifé, R M Ortuño Tetrahedron: Asymmetry 6 1849 (1995)
77. M P Doyle, M N Protopopova Tetrahedron 54 7919 (1998)
78. K El Abdioui, J Martinez, P Viallefont, Y Vidal Bull. Soc. Chim. Belg. 106 425 (1997)
79. R Aumann, B Trentmann, C Krüger, F Lutz Chem. Ber. 124 2595 (1991)
80. T Kurihara, E Kawasaki, K Nasu Heterocycles 20 1913 (1983)
81. T Kurihara, T Tani, K Nasu, M Inoue, T Ishida Chem. Pharm. Bull. 29 3214 (1981)
82. J M Jiménez, R M Ortuño Tetrahedron: Asymmetry 7 3203 (1996)
83. M Tamura, J A Park, C H Stammer Pept. Chem. 705 (1998)
84. E Godier-Marc, D J Aitken, H-P Husson Tetrahedron Lett. 38 4065 (1997)
85. M Díaz, R M Ortuño Tetrahedron: Asymmetry 7 3465 (1996)
86. M Díaz, J M Jiménez, R M Ortuño Tetrahedron: Asymmetry 8 2465 (1997)
87. WO PCT 0009 558; Chem. Abstr. 132 175 808 (2000)