Synthesis of "Garner" aldehyde-derived cyclopropylboronic esters

European Journal of Organic Chemistry

Volumn , Issue 16, 2003, Pages 3219-3229

  Pietruszka, Jörg ^a   Witt, Andreas ^a   Frey, Wolfgang ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Amino acids; Amino alcohols; Boronic esters; Cyclopropanes; Suzuki coupling

Indexed keywords

ALDEHYDE; ALKYNE; AMINO ACID; AMINOALCOHOL; BORONIC ACID DERIVATIVE; CYCLOPROPANE; CYCLOPROPANOL; CYCLOPROPYLBORONIC ESTER; GARNER ALDEHYDE; PROPANOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLOPROPANATION; DIASTEREOISOMER; MATTESON HOMOLOGATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION; SUZUKI COUPLING; SYNTHESIS; X RAY ANALYSIS;

EID: 0041475870     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300220     Document Type: Article

References (92)

1. J. Salaün, Top. Curr. Chem. 2000, 207, 1-67.
2. N. Andres, H. Wolf, H. Zähner, E. Rössner, A. Zeeck, W. A. König, V. Sinnwell, Helv. Chim. Acta 1989, 72, 426-437.
3. E. Rössner, A. Zeeck, W. A. König, Angew. Chem. 1990, 102, 84-85; Angew. Chem. Int. Ed. Engl. 1990, 29, 64.
4. E. Rössner, A. Zeeck, W. A. König, Angew. Chem. 1990, 102, 84-85; Angew. Chem. Int. Ed. Engl. 1990, 29, 64.
5. A. Asai, A. Hasegawa, K. Ochiai, Y. Yamashita, T. Mizukami, J. Antibiot. 2000, 53, 81-83.
6. G. A. Rosenthal, Plant Nonproteinogenic Amino and Imino Acids. Biological and Toxicological Properties, Academic Press, New York, 1982.
7. G. C. Barrett, Chemistry and Biochemistry of the Amino Acids, Chapman and Hall, New York, 1985, pp. 64-95.
8. M. C. Pirrung, G. M. McGeehan, Angew. Chem. 1985, 97, 1074-1075; Angew. Chem. Int. Ed. Engl. 1985, 24, 1044.
9. M. C. Pirrung, G. M. McGeehan, Angew. Chem. 1985, 97, 1074-1075; Angew. Chem. Int. Ed. Engl. 1985, 24, 1044.
10. A. Reichelt, C. Gaul, R. R. Frey, A. Kennedy, S. F. Martin, J. Org. Chem. 2002, 67, 4062-4075.
11. H. R. Plake, T. B. Sundberg, A. R. Woodward, S. F. Martin, Tetrahedron Lett. 2003, 44, 1571-1574.
12. M. C. Hillier, J. P. Davidson, S. F. Martin, J. Org. Chem. 2001, 66, 1657-1671.
13. S. F. Martin, G. O., Dorsey, T. Gane, M. C. Hillier, H. Kessler, M. Baur, B. Mathä, J. Med. Chem. 1998, 41, 1581-1597.
14. S. F. Martin, M. P. Dwyer, B. Hartmann, K. S. Knight, J. Org. Chem. 2000, 65, 1305-1318.
15. M. Martín-Vilà, E. Muray, G. P. Aguado, A. Alvarez-Larena, V. Branchadell, C. Minguillón, E. Giralt, R. M. Ortuño, Tetrahedron: Asymmetry 2000, 11, 3569-3584.
16. K. Shimamoto, M. Ishida, H. Shinozaki, Y. Ohfune, J. Org. Chem. 1991, 56, 4167-4176.
17. S. Nakanishi, Science 1992, 258, 597.
18. H. S. A. Sherratt, in Short-term regulation of liver metabolism (Eds.: L. Hue, G. Van de Werve), Elsevier/North-Holland Biomedical Press, Amsterdam, 1981, pp. 199-227.
19. H. S. A. Sherratt, TIPS 1986, 7, 186-191.
20. J. E. Baldwin, R. M. Adlington, D. Bebbington, A. T. Russell, J. Chem. Soc., Chem. Commun. 1992, 1249-1251.
21. M.-t. Lai, L. Hung-wen, J. Am. Chem. Soc. 1992, 114, 3160-3162.
22. R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, New York, 1989.
23. M. J. O'Donnell (Ed.), 'α-Amino Acid Synthesis, Tetrahedron Symposium in Print Number 33, London, 1988, vol. 44, p. 17.
24. F. P. J. T. Rutjes, L. B. Wolf, H. E. Schoemaker, J. Chem. Soc., Perkin Trans. 1 2000, 4197-4212.
25. R. O. Duthaler, Tetrahedron 1994, 50, 1539-1650.
26. C. Cativiela, M. D. Diaz-de-Villegas, Tetrahedron: Asymmetry 1998, 9, 3317-3599.
27. H. J. C. Deboves, U. Grabowska, A. Rizzo, R. E W. Jackson, J. Chem. Soc., Perkin Trans. 1 2000, 4284-4292.
28. C. S. Dexter, R. F. W. Jackson, J. Elliott, J. Org. Chem. 1999, 64, 7579-7585.
29. R. F. W. Jackson, R. J. Moore, C. S. Dexter, J. Elliot, C. E. Mowbray, J. Org. Chem. 1998, 63, 7875-7884.
30. R. F. W. Jackson. J. L. Fraser, N. Wishart, B. Porter, M. J. Wythes, J. Chem. Soc., Perkin Trans. 1 1998, 1903-1912.
31. M. J. Dunn, R. F. W. Jackson, J. Pietruszka, D. Turner, J. Org. Chem. 1995, 60, 2210-2215.
32. A. D. Campbell, T. M. Raynham, R. J. K. Taylor, Tetrahedron Lett. 1999, 40, 5263-5266.
33. P. N. Collier, A. D. Campbell, I. Patel, T. M. Raynham, R. J. K. Taylor, J. Org. Chem. 2002, 67, 1802-1815.
34. P. N. Collier, A. D. Campbell, I. Patel, R. J. K. Taylor, Tetrahedron 2002, 58, 6117-6125.
35. M. Sabat, C. R. Johnson, Org. Lett. 2000, 2, 1089-1092.
36. R. L. Danheiser, A. C. Savoca, J. Org. Chem. 1985, 50, 2401-2403.
37. P. Fontani, B. Carboni, M. Vaultier, R. Carrié, Tetrahedron Lett. 1989, 30, 4815-4818.
38. T. Imai, H. Mineta, S. Nishida, J. Org. Chem. 1990, 55, 4986-4988.
39. P. Fontani, B. Carboni, M. Vaultier, G. Maas, Synthesis 1991, 605-609.
40. J. P. Hildebrand, S. P. Marsden, Synlett 1996, 893-894.
41. Z. Wang, M.-Z. Deng, J. Chem. Soc., Perkin Trans. 1 1996, 2663-2664.
42. A. B. Charette, R. P. De Freitas-Gil, Tetrahedron Lett. 1997, 38, 2809-2812.
43. J. Pietruszka, M. Widenmeyer, Synlett 1997, 977-979.
44. D. S. Matteson, Stereodirected Synthesis with Organoboranes, Springer-Verlag, Heidelberg, 1995.
45. C. Morin, Tetrahedron 1994, 50, 12521-12569.
46. A. Pelter, K. Smith, H. C. Brown, Borane Reagents, Academic Press, London, 1988.
47. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
48. I. Beletskaya, A. Pelter, Tetrahedron 1997, 53, 4957-5026.
49. D. S. Matteson, Tetrahedron 1998, 54, 10555-10607.
50. A. Suzuki, J. Organomet. Chem. 1999, 576, 147-168.
51. K. Nakayama, J. D. Rainier, Tetrahedron 1990, 46, 4165-4170.
52. J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 1999, 64, 8287-8297.
53. J. E. A. Luithle, J. Pietruszka, Liebigs Ann./Recueil 1997, 2297-2302.
54. J. E. A. Luithle, J. Pietruszka, A. Witt, Chem. Commun. 1998, 2651-2652.
55. J. E. A. Luithle, J. Pietruszka, Eur. J. Org. Chem. 2000, 2557-2562.
56. J. E. A. Luithle, J. Pietruszka, J. Org. Chem. 2000, 65, 9194-9200.
57. J. Pietruszka, A. Witt, J. Chem. Soc., Perkin Trans. 1 2000, 4293-4300.
58. P. Garner, Tetrahedron Lett. 1984, 25, 5855-5858.
59. P. Garner, J. M. Park, J. Org. Chem. 1987, 52, 2361-2364.
60. P. Garner, J. M. Park, Org. Synth. 1991, 70, 18-26.
61. A. Dondoni, D. Perrone, Org. Synth. 1999, 77, 64-77.
62. X. Liang, J. Andersch, M. Bols, J. Chem. Soc., Perkin Trans. 1 2001, 2136-2157.
63. J. Pietruszka, A. Witt, Synlett 2003, 91-94.
64. P. Meffre, L. Gauzy, C. Perdigues, F. Desanges-Levecque, E. Branquet, P. Durand, F. Le Goffic, Tetrahedron Lett. 1995, 36, 877-880.
65. G. T. Crisp, Y.-L. Jiang, P. J. Pullman, C. De Savi, Tetrahedron 1997, 53, 17489-17500.
66. P. Meffre, S. Hermann, P. Durand, G. Reginato, A. Riu, Tetrahedron 2002, 58, 5159-5162.
67. D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155-4156.
68. R. K. Boeckmann, Jr, P. Shao, J. J. Mullins, Org. Synth. 1999, 77, 141-152.
69. A. G. Myers, B. Zhong, M. Movassaghi, D. W. Kung, B. A. Lanman, S. Kwon, Tetrahedron Lett. 2000, 41, 1359-1362.
70. S. Ohira, Synth. Commun. 1989, 19, 561-564.
71. S. Müller, B. Liepold, G. J. Roth, H. J. Bestmann, Synlett 1996, 521-522.
72. M. Kitamura, M. Tokunaga, R. Noyori, J. Am. Chem. Soc. 1995, 117, 2931-2932.
73. J. S. Baum, D. A. Shook, Synth. Commun. 1987, 17, 1709-1716.
74. P. Callant, L. D'Haenens, M. Vandewalle, Synth. Commun. 1984, 14, 155-161.
75. D. G. Brown, E. J. Velthuisen, J. R. Commerford, J. Org. Chem. 1996, 61, 2540-2541.
76. Although the enantiomeric integrity of compound 7 was checked by its optical rotation, only indirect proof was obtained after formation of diastereoisomeric alkenylboronic esters 12 and 13: The corresponding esters ent-13 and ent-12 were not detected.
77. Y.-L. Song, Synlett 2000, 1210.
78. C. E. Tucker, J. Davidson, P. Knochel, J. Org. Chem. 1992, 57, 3482-3485.
79. A. Zhang, Y. Kan, G.-L. Zhao, B. Jiang, Tetrahedron 2000, 56, 965-970.
80. R. W. Hoffmann, S. Dresely, Synthesis 1988, 103-106.
81. A. Kamabuchi, T. Moriya, N. Miyaura, A. Suzuki, Synth. Commun. 1993, 23, 2851-2859.
82. Y. Baba, G. Saha, S. Nakao, C. Iwata, T. Tanaka, T. Ibuka, H. Ohishi, Y. Takemoto, J. Org. Chem. 2001, 66, 81-86.
83. M. P. de Frutos, M. D. Fernández, E. Fernández-Alvarez, M. Bernabé, Tetrahedron 1992, 48, 1123-1130.
84. M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J. J. Grabowski, P. J. Reider, Tetrahedron Lett. 1998, 39, 5323-5326.
85. J. A. Moore, D. E. Reed, Org. Synth., Coll. Vol. V 1973, 351-355.
86. P. Lombardi, Chem. Ind. (London) 1990, 708.
87. S. Moss, Chem. Ind. (London) 1994, 122.
88. For the safe handling of diazomethane with the aid of a syringe-pump, all tubing, fittings and joints were made from Teflon; metals must be omitted.
89. CCDC-206722 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: (internat.) +44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
90. R. Köster, Y. Morita, Justus Liebigs Ann. Chem. 1967, 704, 70-90.
91. G. Zweifel, G. M. Clark, N. L. Polston, J. Am. Chem. Soc. 1971, 93, 3395-3399.
92. J. A. Miller, G. Zweifel, Synthesis 1981, 288-289.