Synthetic studies with carbohydrate-derived chiral auxiliaries

Tetrahedron

Volumn 53, Issue 44, 1997, Pages 14823-14870

  Hultin, Philip G ^a   Earle, Marion A ^a   Sudharshan, Manjula ^a  

^a UNIVERSITY OF MANITOBA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE;

CARBOHYDRATE SYNTHESIS; CHEMICAL MODIFICATION; CHIRALITY; CONFORMATION; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 0030772585     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00766-7     Document Type: Review

References (142)

1. a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281;
2. b) Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Tetrahedron Organic Chemistry Series 12; Elsevier Science Inc.: Tarrytown, N.Y., 1994.
3. Seyden-Penne, J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis; Dennis P. Curran, (Trans.); Wiley: New York, 1995.
4. Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
5. a) Kunz, H.; Rück, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 336-358;
6. b) Hale, K. J. Monosaccharides: Use in synthesis as chiral templates. In Second Supplements to the 2nd Edition of Rodd's Chemistry of Carbon Compounds; Sainsbury, M., Ed.; Elsevier: Amsterdam, 1993; Vol. I EFG, pp. 273-313.
7. Kunz, H. Pure Appl. Chem. 1995, 67, 1627-1635.
8. Bols, M. Carbohydrate Building Blocks; Wiley: New York, 1996.
9. Kunz, H.; Pfrengle, W.; Rück, K.; Sager, W. Synthesis 1991, 1039-1042.
10. DiCesare, J. C. Carbohydrates as chiral auxiliaries in organometallic reactions, Georgia Institute of Technology 1992.
11. Collins, P.; Ferrier, R. J. Monosaccharides: Their Chemistry and Their Roles in Natural Products; Wiley: Chichester, 1995.
12. Kunz, H.; Mohr, J. J. Chem. Soc., Chem. Commun. 1988, 1315-1317.
13. Juaristi, E.; Cuevas, G. The Anomeric Effect; CRC Press: Boca Raton, 1995.
14. Llera, J. M.; Lopez, J. C.; Fraser-Reid, B. J. Org. Chem. 1990, 55, 2997-2998.
15. Senderowitz, H.; Still, W. C. J. Org. Chem. 1997, 62, 1427-1438, and references therein.
16. Giuliano, R. M. Cycloaddition Reactions in Carbohydrate Chemistry; ACS Symposium Series no. 494; American Chemical Society: Washington, 1992.
17. Lubineau, A. Chem. Ind. (London) 1996, 123-126.
18. a) Lubineau, A.; Bienaymé, H.; Queneau, Y.; Scherrmann, M.-C. New J. Chem. 1994, 18, 279-285;
19. b) Lubineau, A.; Bienaymé, H.; Queneau, Y. Carbohydr. Res. 1995, 270, 163-179.
20. Lubineau, A.; Scherrmann, M.-C.; Mentech, J. Eur. Pat. Appl. EP 0 587 471 A1, 16 March 1993, Chem. Abstr., 121:158095.
21. Lubineau, A.; Scherrmann, M.-C.; Mentech, J. Eur. Pat. Appl. EP 0 587 471 A1, 16 March 1993, Chem. Abstr., 121:158095.
22. Beagley, B.; Larsen, D. S.; Pritchard, R. G.; Stoodley, R. J. J. Chem. Soc., Perkin Trans. 1 1990, 311-3127, and previous papers in that series.
23. Lowe, R. F.; Stoodley, R. J. Tetrahedron Lett. 1994, 35, 6351 -6354.
24. Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem., Int. Ed. Engl. 1985, 24, 1-76.
25. Aspinall, I. H.; Cowley, P. M.; Mitchell, G.; Stoodley, R. J. J. Chem. Soc., Chem. Commun. 1993, 1179-1180.
26. Aspinall, I. H.; Cowley, P. M.; Stoodley, R. J.; Mitchell, G. Tetrahedron Lett. 1994, 35, 3397-3400.
27. Shing, T. K. M.; Chow, H.-F.; Chung, I. H. F. Tetrahedron Lett. 1996, 37, 3713-3716.
28. Gras, J.-L.; Poncet, A.; Nouguier, R. Tetrahedron Lett. 1992, 33, 3323-3326.
29. Nouguier, R.; Gras, J.-L.; Giraud, B.; Virgili, A. Tetrahedron 1992, 48, 6245-6252.
30. Nouguier, R.; Mignon, V.; Gras, J.-L. Carbohydr. Res. 1995, 277, 339-345.
31. Akiyama, T.; Horiguchi, N.; Ida, T.; Ozaki, S. Chem. Lett. 1995, 975-976.
32. Loupy, A.; Monteux, D. Tetrahedron Lett. 1996, 37, 7023-7026.
33. a) Cadogan, J. I. G.; Hodgson, P. K. G.; Gosney, I.; Banks, M. R. U.K. Pat. Appl. GB 2 261 435 A, 13 November 1992, Chem. Abstr., 121:180109;
34. a) Cadogan, J. I. G.; Hodgson, P. K. G.; Gosney, I.; Banks, M. R. U.K. Pat. Appl. GB 2 261 435 A, 13 November 1992, Chem. Abstr., 121:180109;
35. b) Banks, M. R.; Blake, A. J.; Cadogan, J. I. G.; Dawson, I. M.; Gaur, S.; Gosney, I.; Gould, R. O.; Grant, K. J.; Hodgson, P. K. G. J. Chem Soc., Chem. Commun. 1993, 1146-1148;
36. c) Banks, M. R.; Cadogan, J. I. G.; Gosney, I.; Gaur, S.; Hodgson, P. K. G. Tetrahedron: Asymmetry 1994, 5, 2447-2458.
37. Beagley, B.; Curtis, A. D. M.; Pritchard, R. G.; Stoodley, R. J. J. Chem. Soc., Perkin Trans, 1 1992, 1981-1991.
38. Cousins, R. P.; Curtis, A. D. M.; Ding, W. C.; Stoodley, R. J. Tetrahedron Lett. 1995, 36, 8689-8692.
39. Braun, H.; Felber, H.; Kresze, G.; Schmidtchen, F. P.; Prewo, R.; Vasella, A. Liebigs Ann. Chem. 1993, 261-268.
40. Defoin, A.; Sarazin, H.; Streith, J. Helv. Chim. Acta 1996, 79, 560-567.
41. a) Horton, D.; Koh, D. Tetrahedron Lett. 1993, 34, 2283-2286;
42. b) Horton, D.; Koh, D.; Takagi, Y. Carbohydr. Res. 1993, 250, 261-274.
43. Horton, D.; Koh, D. Carbohydr. Res. 1993, 250, 249-260.
44. a) Serrano, J. A.; Moreno, M. Ch.; Román, E.; Arjona, O.; Plumet, J.; Jiménez, J. J. Chem. Soc., Perkin Trans, 1 1991, 3207-3212;
45. b) Serrano, J. A.; Cáceres, L. E.; Román, E. J. Chem. Soc., Perkin Trans, 1 1995, 1863-1871.
46. Galan, E. R.; Hodgson, D. J.; Yokomori, Y.; Eliel, E. L.; Martinez, M. B.; Serrano Blazquez, J. A. Carbohydr. Res. 1988, 180, 263-276.
47. Franck, R. W. Carbohydrate dienophiles in [4+2] cycloadditions. In Cycloaddition Reactions in Carbohydrate Chemistry; ACS Symposium Series no. 494; Giuliano, R. M., Ed.; American Chemical Society: Washington, 1992; pp. 24-32.
48. Ganz, I.; Kunz, H. Synthesis 1994, 1353-1358.
49. a) Kaluza, Z.; Furman, B.; Patel, M.; Chmielewski, M. Tetrahedron: Asymmetry 1994, 5, 2179-2186;
50. b) Furman, B.; Kaluza, Z.; Chmieleski, M. Tetrahedron 1996, 52, 6019-6024;
51. c) Kaluza, Z.; Furman, B.; Chmielewski, M. Tetrahedron: Asymmetry 1995, 6, 1719-1730.
52. Anaya, J.; Barton, D. H. R.; Gero, S. D.; Grande, M.; Hernando, J. I. M.; Laso, N. M. Tetrahedron: Asymmetry 1995, 6, 609-624.
53. a) Charette, A. B.; Côté, B.; Marcoux, J.-F. J. Am. Chem. Soc. 1991, 113, 8166-8167;
54. b) Charette, A. B.; Côté, B. J. Org. Chem. 1993, 58, 933-936;
55. c) Charette, A.B.; Marcoux, J.-F. Synlett 1995, 1197-1207.
56. Charette, A. B.; Côté, B. J. Am. Chem. Soc. 1995, 117, 12721-12732.
57. Charette, A. B.; Juteau, H.; Lebel, H.; Deschênes, D. Tetrahedron Lett. 1996, 37, 7925-7928.
58. Kang, J.; Lim, G. J.: Yoon, S. K.: Kim, M. Y. J. Org. Chem. 1995, 60, 564-577.
59. Reissig, H.-U.; Schumacher, R. Synlett 1996, 1121-1122.
60. Chastanet, J.; Fathallah, H.; Negron, G.; Roussi, G. Heterocycles 1992, 34, 1565-1572.
61. Tamura, O.; Mita, N.; Kusaka, N.; Suzuki, H.; Sakamoto, M. Tetrahedron Lett. 1997, 38, 429-432.
62. Fišera, L.; Al-Timari, U. A. R.; Ertl, P.; Prónayova, N. Monatsh. Chem. 1993, 124, 1019-1029.
63. a) Avalos, M.; Babiano, R.; Cabanillas, A.; Cintas, P.; Diánez, M. J.; Estrada, M. D.; Jiménez, J. L.; López-Castro, A.; Palacios, J. C.; Garrido, S. P. J. Chem. Soc., Chem. Commun. 1995 , 2213-2214;
64. b) Avalos, M.; Babiano, R.; Cabanillas, A.; Cintas, P.; Higes, F. J.; Jiménez, J. L.; Palacios, J. C. J. Org. Chem. 1996, 61, 3738-3748.
65. Martín, N.; Martínez-Grau, A.; Seoane, C.; Marco, J. L. Tetrahedron: Asymmetry 1995, 6, 255-262.
66. a) Rück, K.; Kunz, H. Synthesis 1993, 1018-1028;
67. b) Rück-Braun, K.; Stamm, A.; Engel, S.; Kunz, H. J. Org. Chem. 1997, 62, 967-975.
68. a) Garner, P. P.; Cox, P. B.; Klippenstein, S. J. J. Am. Chem. Soc. 1995, 117, 4183-4184;
69. b) Garner, P.; Leslie, R.; Anderson, J. T. J. Org. Chem. 1996, 61, 6754-6755.
70. Heathcock, C. H. Modern enolate chemistry: Regio-and stereoselective formation of enolates and the consequence of enolate configuration on subsequent reactions. In Modern Synthetic Methods 1992; Scheffold, R., Ed.; VCH: Weinheim, 1992, pp. 1-102.
71. To avoid ambiguity when discussing the stereochemistry of ester (and imide) enolates, we will follow Evans (Evans, D.A. Stereoselective Alkylation Reactions of Chiral Metal Enolates. In Asymmetric Synthesis, Vol. 3, Morrison, J.E. Ed.; Academic Press: Orlando, 1984; pg. 11) in assigning a higher priority to the negatively charged enolate oxygen than to the alkoxy (or amido) group, regardless of the identity of the metal counter-ion. The reader should be aware that the authors cited may not have followed this convention in their original publications.
72. a) Evans, D. A.; Bartroli, J.; Shih, T. L. J. Am. Chem. Soc. 1981, 103, 2127-2129;
73. b) Nerz-Stormes, M.; Thornton, E. R. J. Org. Chem. 1991, 56, 2489-2498;
74. c) Evans, D. A.; Clark, J. S.; Metternich, R.; Novack, V. J.; Sheppard, G. S. J. Am. Chem. Soc. 1990, 112, 866-868.
75. a) Costa, P. R. R.; Ferreira, V. F.; Alencar, K. G.; Filho, H. C. A.; Ferreira, C. M.; Pinheiro, S. J. Carbohydr. Chem. 1996, 15, 691-699;
76. b) Costa, P. R. R.; Ferreira, V. F.; Filho, H. C. A.; Pinheiro, S. J. Braz. Chem. Soc. 1996, 7, 67-73.
77. Kishida, M.; Eguchi, T.; Kakinuma, K. Tetrahedron Lett. 1996, 37, 2061-2062.
78. Mulzer, J.; Hiersemann, M.; Buschmann, J.; Luger, P. Liebigs Ann.Chem. 1996, 649-654.
79. Keynes, M. N.; Earle, M. A.; Sudharshan, M.; Hultin, P. G. Tetrahedron 1996, 52, 8685-8702.
80. Earle, M. A.; Hultin, P. G. unpublished results, University of Manitoba 1996.
81. a) Köll, P.; Lützen, A. Tetrahedron: Asymmetry 1995, 6, 43-46;
82. b) Köll, P.; Lützen, A. Tetrahedron: Asymmetry 1996, 7, 637-640;
83. c) Lützen, A.; Köll, P. Tetrahedron: Asymmetry 1997, 8, 29-32.
84. Angibaud. P.; Chaumette, J. L.; Desmurs, J. R.; Duhamel, L.; Plé, G.; Valnot, J. Y.; Duhamel, P. Tetrahedron: Asymmetry 1995, 6, 1919-1932.
85. Lützen, A.; Köll, P. Tetrahedron: Asymmetry 1997, 8, 1193-1206.
86. O'Donnell, M. J.; Wu, S.; Huffman, J. C. Tetrahedron 1994, 50, 4507-4518.
87. Solladié, G.; Saint Clair, J.-F.; Philippe, M.; Semeria, D.; Maignan, J. Tetrahedron: Asymmetry 1996, 7, 2359-2364.
88. Akiyama, T.; Ishikawa, K.; Ozaki, S. Synlett 1994, 275-276.
89. a) Nangia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Synop. 1996, 312-313;
90. b) Nangia, A.; Rao, P. B.; Madhavi, N. N. L. J. Chem. Res., Miniprint 1996, 1716-1730.
91. Kunz, H.; Burgard, A.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 386-387.
92. Kunz, H.; Schanzenbach, D. Angew. Chem., Int. Ed. Engl. 1989, 28, 1068-1069.
93. Gennari, C. Asymmetric synthesis with enol ethers. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon: Oxford, 1991; Vol. 2, pp. 629-660.
94. Lehnhoff, S.; Goebel, M.; Karl, R. M.; Klösel, R.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 1104-1107.
95. Roush, W. R.; VanNieuwenhze, M. S. J. Am. Chem. Soc. 1994, 116, 8536-8543.
96. Yamamoto, Y.; Kobayashi, K.; Okano, H.; Kadota, I. J. Org. Chem. 1992, 57, 7003-7005.
97. Shing, T. K. M.; Li, L.-H. J. Org. Chem. 1997, 62, 1230-1233.
98. Rochet, P.; Vatèle, J.-M.; Goré, J. Synlett 1993, 105-107.
99. a) Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F.; Merino, P.; Tejero, T. Synth. Commun. 1994, 24, 2537-2550;
100. b) Dondoni, A.; Franco, S.; Junquera, F.; Merchán, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J. 1995, 1, 505-520.
101. a) Rohloff, J. C.; Alfredson, T. V.; Schwartz, M. A. Tetrahedron Lett. 1994, 35, 1011-1014;
102. b) Basha, A.; Henry, R.; McLaughlin, M. A.; Ratajczyk, J. D.; Wittenburger, S. J. J. Org. Chem. 1994, 59, 6103-6106.
103. Huber, R.; Vasella, A. Tetrahedron 1990, 46, 33-58.
104. Zhang, W. Y.; Lantos, I.; Matsuoka, R. T.; Mendelson, W.; Webb, K.; Tucker, L. M.; Liu, L.; Procter, G. PCT Int. Appl. WO 9619438 A1, 27 June 1996, Chem. Abstr., 125:142537.
105. Zhang, W. Y.; Lantos, I.; Matsuoka, R. T.; Mendelson, W.; Webb, K.; Tucker, L. M.; Liu, L.; Procter, G. PCT Int. Appl. WO 9619438 A1, 27 June 1996, Chem. Abstr., 125:142537.
106. a) Idris, M. S.; Larsen, D. S.; Schofield, A.; Stoodley, R. J.; Tiffin, P. D. Tetrahedron Lett. 1995, 36, 3251-3254;
107. b) Larsen, D. S.; Schofield, A.; Stoodley, R. J.; Tiffin, P. D. Tetrahedron Lett. 1994, 35, 9285-9288.
108. DiCesare, J. C.; McDougal, P. G. Abstracts of Papers; 212th National Meeting; American Chemical Society: Washington, DC, 1996; ORGN 376.
109. Maeda, Y; Tago, K.; Eguchi, T.; Kakinuma, K. Biosci., Biotechnol., Biochem. 1996, 60, 1248-1254.
110. Charette, A. B.; Côté, B. Tetrahedron: Asymmetry 1993, 4, 2283-2286.
111. Gurjar, M. K.; Mainkar, A. S. Tetrahedron: Asymmetry 1992, 3, 21-24.
112. Bellucci, G.; Chiappe, C.; D'Andrea, F. Tetrahedron: Asymmetry 1995, 6, 221-230.
113. Akiyama, T.; Nishimoto, H.; Kuwata, T.; Ozaki, S. Bull. Chem. Soc. Jpn. 1994, 67, 180-188.
114. Nair, V.; Prabhakaran, J. J. Chem. Soc., Perkin Trans, 1 1996, 593-594.
115. Zimmer, R.; Arnold, T.; Homann, K.; Reissig, H.-U. Synthesis 1994, 1050-1056.
116. Watanabe, Y.; Ono, Y.; Hayashi, S.; Ueno, Y.; Toru, T. J. Chem. Soc., Perkin Trans. 1 1996, 1879-1885.
117. Llera, J. M.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1991, 32, 7299-7302.
118. a) Fernández, I.; Khiar, N.; Llera, J. M.; Alcudia, F. J. Org. Chem. 1992, 57, 6789-6796;
119. b) Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron Lett. 1994, 35, 5719-5722;
120. c) Arroyo-Gómez, Y.; López-Sastre, J. A.; Rodríguez-Amo, J. F.; Santos-Garcia, M.; Sanz-Tejedor, M. A. J. Chem. Soc., Perkin Trans. 1 1994, 2177-2180.
121. El Ouazzani, H.; Khiar, N.; Fernández, I.; Alcudia, F. J. Org. Chem. 1997, 62, 287-291.
122. a) Kolodiazhnyi, O. I. Russ. J. Gen. Chem. 1995, 65, 1769-1770;
123. b) Kolodiazhnyi, O. I.; Grishkun, E. V. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 115, 115-124;
124. c) Kolodiazhnyi, O. I.; Grishkun, E. V. Tetrahedron: Asymmetry 1996, 7, 967-970.
125. Benabra, A.; Alcudia, A.; Khiar, N.; Fernández, I.; Alcudia, F. Tetrahedron: Asymmetry 1996, 7, 3353-3356.
126. a) Kakinuma, K.; Koudate, T.; Li, H.-Y.; Eguchi, T. Tetrahedron Lett. 1991, 32, 5801-5804;
127. b) Eguchi, T.; Koudate, T.; Kakinuma, K. Tetrahedron 1993, 49, 4257-4540.
128. a) Kakinuma, K.; Li, H.-Y. Tetrahedron Lett. 1989, 30, 4157-4160;
129. b) Kakinuma, K.; Terasawa, H.; Li, H.-Y.; Miyazaki, K.; Oshima, T. Biosci., Biotechnol., Biochem. 1993, 57, 1916-1923.
130. Tomooka, K.; Nakamura, Y.; Nakai, T. Synlett 1995, 321-322.
131. Lubineau, A.; Augé, J.; Bellanger, N.; Caillebourdin, S. J. Chem. Soc., Perkin Trans. 1 1992, 1631-1636.
132. Piva, O.; Pete, J.-P. Tetrahedron: Asymmetry 1992, 3, 759-768.
133. a) Piva, O.; Caramelle, D. Tetrahedron: Asymmetry 1995, 6, 831-832;
134. b) Piva, O. J. Org. Chem. 1995, 60, 7879-7883.
135. a) Tochtermann, W.; Schlösser, U.; Popp, B.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Tetrahedron Lett. 1989, 30, 6855-6858;
136. b) Tochtermann, W.; Schlösser, U.; Ott, F.; Popp, B.; Sdunnus, N.; Snatzke, G.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Chem. Ber. 1993, 126, 1733-1742.
137. Banik, B. K.; Manhas, M. S.; Bose, A. K. J. Org. Chem. 1994, 59, 4714-4716.
138. Narasaka, K.; Hidai, E.; Hayashi, Y.; Gras, J.-L. J. Chem. Soc., Chem. Commun. 1993, 102-104.
139. a) Itoh, T.; Chika, J. J. Org. Chem. 1995, 60, 4968-4969;
140. b) Itoh, T.; Chika, J.; Shirakami, S.; Ito, H.; Yoshida, T.; Kubo, Y.; Uenishi, J. J. Org. Chem. 1996, 61, 3700-3705.
141. a) Feldman, K. S.; Ensel, S. M. J. Am. Chem. Soc. 1994, 115, 1162-1163;
142. b) Feldman, K. S.; Ensel, S. M.; Minard, R. D. J. Am. Chem. Soc. 1994, 116, 1742-1745.