Boron-substituted building blocks in Diels-Alder and other cycloaddition reactions

Synthesis

Volumn , Issue 13, 2005, Pages 2091-2115

  Hilt, Gerhard ^a   Bolze, Patrick ^a  

^a PHILIPPS UNIVERSITY MARBURG   (Germany)

Author keywords

1,3 dipole; Boron; Cycloaddition; Cyclotrimerisation; Diels Alder reaction

Indexed keywords

ADDITION REACTIONS; ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

1,3-DIPOLE; CYCLOADDITION; CYCLOTRIMERIZATION; DIELS-ALDER ADDITION;

BORON;

(5R,6S) 6 ACETOXY 5 HEXADECANOLIDE; 1,3 DIENE; ALDEHYDE; ALKADIENE; ALKENYL GROUP; ALKYNYL GROUP; AZOMETHINE YLIDE; BORON; BORONIC ACID DERIVATIVE; CHROMIUM; CYCLOHEXENE DERIVATIVE; HYDRAZONE DERIVATIVE; LEWIS ACID; METHYL PALUSTRAMATE; NATURAL PRODUCT; NITRILE OXIDE; NITRONE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRAN DERIVATIVE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

CATALYSIS; CROSS COUPLING REACTION; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; DIHYDROXYLATION; ENANTIOSELECTIVITY; HYDROBORATION; HYDROLYSIS; OXIDATION; REVIEW; STEREOCHEMISTRY; SUZUKI REACTION; SYNTHESIS;

EID: 23944465006     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-872084     Document Type: Review

References (154)

1. (a) Albrecht, K.; Kaufmann, D. In Science of Synthesis (Houben-Weyl), Vol. 6; Thieme: New York, 2004, 697.
2. (b) Vaultier, M.; Alcaraz, G. In Science of Synthesis (Houben-Weyl), Vol. 6; Thieme: New York, 2004, 721.
3. (c) Miyaura, N. Top. Curr. Chem. 2002, 219, 11.
4. (d) Vaultier, M.; Lorvelec, G.; Plunian, W.; Paulus, O.; Bouju, P.; Mortier, J. Royal Soc. Chem. 2000, 253, 464.
5. (e) Matteson, D. S. In Stereodirected Synthesis with Organoboranes; Springer: Berlin, 1995.
6. (f) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
7. (g) Matteson, D. S. Tetrahedron 1989, 45, 1859.
8. Vaultier, M.; Truchet, F.; Carboni, B.; Hoffmann, R. W.; Denne, I. Tetrahedron Lett. 1987, 28, 4169.
9. Mazal, C.; Vaultier, M. Tetrahedron Lett. 1994, 35, 3089.
10. Mikhailov, B. M.; Cherkasova, K. L. Zh. Obshch. Khim. 1972, 42, 138.
11. Mikhailov, B. M.; Cherkasova, K. L. Zh. Obshch. Khim. 1972, 42, 1744.
12. Renard, P.-Y.; Six, Y.; Lallemand, J.-Y. Tetrahedron Lett. 1997, 38, 6589.
13. Renard, P.-Y.; Lallemand, J.-Y. Tetrahedron: Asymmetry 1996, 7, 2523.
14. Garnier, L.; Plunian, B.; Mortier, J.; Vaultier, M. Tetrahedron Lett. 1996, 37, 6699.
15. Gao, X.; Hall, D. G. Tetrahedron Lett. 2003, 44, 2231.
16. Wang, X. J. Chem. Soc., Chem. Commun. 1991, 1515.
17. Zhang, A.; Kan, Y.; Jiang, B. Tetrahedron 2001, 57, 2305.
18. Mortier, J.; Vaultier, M.; Plunian, B.; Toupet, L. Heterocycles 1999, 50, 703.
19. Renard, P.-Y.; Lallemand, J.-Y. Bull. Soc. Chim. Fr. 1996, 133, 143.
20. Ohanessian, G.; Six, Y.; Lallemand, J.-Y. Bull. Soc. Chim. Fr. 1996, 133, 1143.
21. Six, Y.; Lallemand, J.-Y. Tetrahedron Lett. 1999, 40, 1295.
22. Lallemand, J.-Y.; Six, Y.; Ricard, L. Eur. J. Org. Chem. 2002, 503.
23. Jehanno, E.; Vaullier, M. Tetrahedron Lett. 1995, 36, 4439.
24. Rasset-Deloge, C.; Martinez-Fresneda, P.; Vaultier, M. Bull. Soc. Chim. Fr. 1992, 129, 285.
25. Deligny, M.; Carreaux, F.; Carboni, B.; Toupet, L.; Dujardin, G. Chem. Commun. 2003, 276.
26. Deligny, M.; Carreaux, F.; Toupet, L.; Carboni, B. Adv. Synth. Catal. 2003, 345, 1215.
27. Gao, X.; Hall, D. G. J. Am. Chem. Soc. 2003, 125, 9308.
28. Gao, X.; Hall, D. G. J. Am. Chem. Soc. 2005, 127, 1628.
29. Stierle, D. B.; Stierle, A. A. Experientia 1992, 48, 1165.
30. Tailor, J.; Hall, D. G. Org. Lett. 2000, 2, 3715.
31. Touré, B. B.; Hoveyda, H. R.; Tailor, J.; Ulaczyk-Lesanko, A.; Hall, D. G. Chem.-Eur. J. 2003, 9, 466.
32. Touré, B. B.; Hall, D. G. J. Org. Chem. 2004, 69, 8429.
33. Touré, B. B.; Hall, D. G. Angew. Chem. Int. Ed. 2004, 43, 2001;
34. Angew. Chem. 2004, 116, 2035.
35. Guennouini, N.; Rasset-Deloge, C.; Carboni, B.; Vaultier, M. Synlett 1992, 581.
36. Kamabuchi, A.; Miyaura, N.; Suzuki, A. Tetrahedron Lett. 1993, 34, 4827.
37. Carreaux, F.; Possémé, F.; Carboni, B.; Arrieta, A.; Lecea, B.; Cossío, F. P. J. Org. Chem. 2002, 67, 9153.
38. Shimizu, M.; Kurahashi, T.; Hiyama, T. Synlett 2001, 1006.
39. Kurahashi, T.; Hata, T.; Masai, H.; Kitagawa, H.; Shimizu, M.; Hiyama, T. Tetrahedron 2002, 58, 6381.
40. Waas, J. R.; Sidduri, A.; Knochel, P. Tetrahedron Lett. 1992, 33, 3717.
41. Renaud, J.; Graf, C.-D.; Oberer, L. Angew. Chem. Int. Ed. 2000, 39, 3101;
42. Angrew. Chem. 2000, 112, 3231.
43. Wrackmeyer, B.; Milius, W.; Bhatti, M. H.; Ali, S. J. Organomet. Chem. 2003, 665, 196.
44. Kaufmann, D. E. Chem. Ber. 1987, 120, 901.
45. Kaufmann, D. E.; Schacht, W. Chem. Ber. 1987, 120, 1331.
46. Eisch, J. J.; Kotowicz, B. W. Eur. J. Inorg. Chem. 1998, 761.
47. Matteson, D. S.; Wasserbillig, J. O. J. Org. Chem. 1963, 28, 366.
48. Matteson, D. S.; Talbot, M. L. J. Am. Chem. Soc. 1967, 89, 1123.
49. Woods, W. G.; Bengelsdorf, I. S. J. Org. Chem. 1966, 31, 2769.
50. Evans, D. A.; Scott, W. L.; Truesdale, L. K. Tetrahedron Lett. 1972, 2, 121.
51. Bonk, J. D.; Avery, M. A. Tetrahedron: Asymmetry 1997, 8, 1149.
52. Singleton, D. A.; Martinez, J. P. J. Am. Chem. Soc. 1990, 112, 7423.
53. Singleton, D. A.; Martinez, J. P.; Ndip, G. M. J. Org. Chem. 1992, 57, 5768.
54. Singleton, D. A.; Martinez, J. P.; Watson, J. V.; Ndip, G. M. Tetrahedron 1992, 48, 5831.
55. Singleton, D. A.; Martinez, J. P.; Watson, J. V. Tetrahedron Lett. 1992, 33, 1017.
56. Singleton, D. A.; Martinez, J. P. Tetrahedron Lett. 1991, 32, 7365.
57. Coindard, G.; Braun, J. Bull. Soc. Chim. Fr. 1972, 817.
58. Singleton, D. A.; Kim, K.; Martinez, J. P. Tetrahedron Lett. 1993, 34, 3071.
59. Jego, J.-M.; Carboni, B.; Youssofi, A.; Vaultier, M. Synlett 1993, 595.
60. Noiret, N.; Youssofi, A.; Carboni, B.; Vaultier, M. J. Chem. Soc., Chem. Commun. 1992, 1105.
61. Lee, Y.-K.; Singleton, D. A. J. Org. Chem. 1997, 62, 2255.
62. Singleton, D. A. J. Am. Chem. Soc. 1992, 114, 6563.
63. Silva, M. A.; Pellegrinet, S. C.; Goodman, J. M. Arkivoc 2003, x, 556.
64. Pellegrinet, S. C.; Silva, M. A.; Goodman, J. M. J. Am. Chem. Soc. 2001, 123, 8832.
65. Pellegrinet, S. C.; Silva, M. A.; Goodman, J. M. J. Comput. Aided Mol. Des. 2004, 18, 209.
66. Singleton, D. A.; Redman, A. M. Tetrahedron Lett. 1994, 35, 509.
67. Singleton, D. A.; Leung, S.-W. J. Organomet. Chem. 1997, 544, 157.
68. Martinez-Fresneda, P.; Vaultier, M. Tetrahedron Lett. 1989, 30, 2929.
69. Rasset, C.; Vaultier, M. Tetrahedron 1994, 50, 3397.
70. Lorvelec, G.; Vaultier, M. Tetrahedron Lett. 1998, 39, 5185.
71. Singleton, D. A.; Lee, Y.-K. Tetrahedron Lett. 1995, 36, 3473.
72. Batey, R. A.; Lin, D.; Wong, A.; Hayhoe, C. L. S. Tetrahedron Lett. 1997, 38, 3699.
73. Batey, R. A.; Thadani, A. N.; Lough, A. J. Chem. Commun. 1999, 475.
74. Batey, R. A.; Thadani, A. N.; Lough, A. J. J. Am. Chem. Soc. 1999, 121, 450.
75. Narasaka, K.; Yamamoto, I. Tetrahedron 1992, 48, 5743.
76. Yamamoto, I.; Narasaka, K. Bull. Chem. Soc. Jpn. 1994, 67, 3327.
77. Blanchard, C.; Framery, E.; Vaultier, M. Synthesis 1996, 45.
78. Brown, H. C.; Bhat, N. G.; Srebnik, M. Tetrahedron Lett. 1988, 29, 2631.
79. For a review on the chemistry of alkynyl boronates, see: Negishi, E. In Comprehensive Organometallic Chemistry, Vol. 7; Wilkinson, G.; Stone, F. G. A.; Abel, E. W., Eds.; Pergamon: Oxford, 1983, 337.
80. Matteson, D. S.; Peacock, K. J. Am. Chem. Soc. 1960, 82, 5759.
81. Matteson, D. S. J. Org. Chem. 1962, 27, 4293.
82. Seitz, G.; Haenel, F. Arch. Pharm. 1994, 327, 673.
83. Leung, S.-W.; Singleton, D. A. J. Org. Chem. 1997, 62, 1955.
84. Singleton, D. A.; Leung, S.-W. J. Org. Chem. 1992, 57, 4796.
85. Early calculations on a RHF/3-21G level were consistent with the observed chemical behavior; compare ref. 76.
86. Silva, M. A.; Pellegrinet, S. C.; Goodman, J. M. J. Org. Chem. 2003, 68, 4059.
87. Silva, M. A.; Pellegrinet, S. C.; Goodman, J. M. J. Org. Chem. 2002, 67, 8203.
88. Silva, M. A.; Goodman, J. M. Tetrahedron Lett. 2003, 44, 8233.
89. (a) Davies, M. W.; Johnson, C. N.; Harrity, J. P. A. Chem. Commun. 1999, 2107.
90. (b) For a recent review, see: Dötz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187.
91. Yamashita, A.; Tay, A. Tetrahedron Lett. 1986, 27, 3471.
92. Davies, M. W.; Johnson, C. N.; Harrity, J. P. A. J. Org. Chem. 2001, 66, 3525.
93. (a) Vollhardt, K. P. C.; Eichberg, M. J. In Strategies and Tactics in Organic Synthesis; Elsevier: London, 2004, 365.
94. (b) Varela, J. A.; Saa, C. Chem. Rev. 2003, 103, 3787.
95. (c) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
96. (d) Vollhardt, K. P. C. Lect. Heterocycl. Chem. 1987, 9, 59.
97. Gu, Y.; Pritzkow, H.; Siebert, W. Eur. J. Inorg. Chem. 2001, 373.
98. Goswami, A.; Maier, C.-J.; Pritzkow, H.; Siebert, W. Eur. J. Org. Chem. 2004, 2635.
99. Gandon, V.; Leca, D.; Aechtner, T.; Vollhardt, K. P. C.; Malacria, M.; Aubert, C. Org. Lett. 2004, 6, 3405.
100. Ester, C.; Maderna, A.; Pritzkow, H.; Siebert, W. Eur. J. Inorg. Chem. 2000, 1177.
101. Yamamoto, Y.; Ishii, J.-i.; Nishiyama, H.; Itoh, K. J. Am. Chem. Soc. 2004, 126, 3712.
102. Hilt, G.; Smolko, K. I. Angew. Chem. 2003, 115, 2901;
103. Angew. Chem. Int. Ed. 2003, 42, 2795.
104. Hilt, G.; Hess, W.; Schmidt, F. Eur. J. Org. Chem. 2005, in press.
105. Hilt, G.; Lüers, S.; Smolko, K. I. Org. Lett. 2005, 7, 251.
106. Jazouli, M.; Carboni, B.; Carrié, R.; Soufiaoui, M.; Toupet, L. Heteroat. Chem. 1994, 5, 513.
107. Wallace, R. H.; Zong, K. K. Tetrahedron Lett. 1992, 33, 6941.
108. Bast, K.; Christl, M.; Huisgen, R.; Mack, W.; Sustmann, R. Chem. Ber. 1973, 106, 3258.
109. Mukaiyama, T.; Hoshimo, T. J. Am. Chem. Soc. 1960, 82, 5339.
110. Jazouli, M.; Baba, S.; Carboni, B.; Carrié, R.; Soufiaoui, M. J. Organomet. Chem. 1995, 498, 229.
111. Wallace, R. H.; Liu, J. Tetrahedron Lett. 1994, 35, 7493.
112. Grünanger, P.; Vita-Finzi, P. In Isoxazoles, Vol. 49, Part 1; Wiley: New York, 1991, 417.
113. Wallace, R. H.; Liu, J.; Zong, K. K.; Eddings, A. Tetrahedron Lett. 1997, 38, 6791.
114. Lui, J.; Eddings, A.; Wallace, R. H. Tetrahedron Lett. 1997, 38, 6795.
115. Zhang, A.; Kan, Y.; Zhao, G.-L.; Jiang, B. Tetrahedron 2000, 56, 965.
116. Wallace, R. H.; Zong, K. K. J. Organomet. Chem. 1999, 581, 87.
117. Davies, C. D.; Marsden, S. P.; Stokes, E. S. E. Tetrahedron Lett. 1998, 39, 8513.
118. Davies, C. D.; Marsden, S. P.; Stokes, E. S. E. Tetrahedron Lett. 2000, 41, 4229.
119. Jiang, B.; Zhang, A.; Ying, K. Chin. J. Chem. 1999, 17, 293.
120. Bianchi, G.; Cogoli, A.; Grünanger, P. J. Organomet. Chem. 1966, 6, 598.
121. Davies, M. W.; Wybrow, R. A. J.; Johnson, C. N.; Harrity, J. P. A. Chem. Commun. 2001, 1558.
122. Moore, J. E.; Goodenough, K. M.; Spinks, D.; Harrity, J. P. A. Synlett 2002, 2071.
123. Carboni, B.; Ollivault, M.; Le Bouguenec, F.; Carrié, R.; Jazouli, M. Tetrahedron Lett. 1997, 38, 6665.
124. Belfaitah, A.; Isly, M.; Carboni, B. Tetrahedron Lett. 2004, 45, 1969.
125. Rastelli, A.; Gandolfi, R.; Sarzi-Amade, M.; Carboni, B. J. Org. Chem. 2001, 66, 2449.
126. Sáez, J.; Arnó, M.; Domingo, L. R. Tetrahedron 2003, 59, 9167.
127. Micalizio, G. C.; Schreiber, S. L. Angew. Chem. Int. Ed. 2002, 41, 152;
128. Angew. Chem. 2002, 114, 160.
129. Micalizio, G. C.; Schreiber, S. L. Angew. Chem. Int. Ed. 2002, 41, 3272;
130. Angew. Chem. 2002, 114, 3406.
131. Pietruska, J.; Witt, A. J. Chem. Soc., Perkin Trans. 1 2000, 4293.
132. Markó, I. E.; Kumamoto, T.; Giard, T. Adv. Synth. Catal. 2002, 344, 1063.
133. Markó, I. E.; Giard, T.; Sumida, S.; Gies, A.-E. Tetrahedron Lett. 2002, 43, 2317.
134. Matteson, D. S.; Schaumberg, G. D. J. Org. Chem. 1966, 31, 726.
135. Bubnov, Y. N.; Nesmeyanova, O. A.; Rudashevkaya, T. Y.; Mikhailov, B. M.; Kazansky, B. A. Tetrahedron Lett. 1971, 24, 2153.
136. Little, R. D.; Bode, H.; Stone, K. J.; Wallquist, O.; Dannecker, R. J. Org. Chem. 1985, 50, 2401.
137. Fontani, P.; Carboni, B.; Vaultier, M.; Carrié, R. Tetrahedron Lett. 1989, 30, 4815.
138. Fontani, P.; Carboni, B.; Vaultier, M.; Maas, G. Synthesis 1991, 605.
139. Imai, T.; Mineta, H.; Nishida, S. J. Org. Chem. 1990, 55, 4986.
140. (a) Luithle, J. E. A.; Pietruszka, J. Liebigs Ann./Recl. 1997, 2297.
141. (b) Pietruszka, J.; Widenmeyer, M. Synlett 1997, 977.
142. (c) Luithle, J. E. A.; Pietruszka, J.; Witt, A. Chem. Commun. 1998, 2651.
143. (d) Luithle, J. E. A.; Pietruszka, J. J. Org. Chem. 1999, 64, 8287.
144. (e) Luithle, J. E. A.; Pietruszka, J. J. Org. Chem. 2000, 65, 9194.
145. (a) Wang, X.-Z.; Deng, M.-Z. J. Chem. Soc., Perkin Trans. 1 1996, 2663.
146. (b) Zhou, S.-M.; Yan, Y.-L.; Deng, M.-Z. Synlett 1998, 198.
147. (c) Zhou, S.-M.; Deng, M.-Z.; Xia, L.-J.; Tang, M.-H. Angew. Chem. Int. Ed. 1998, 37, 2845;
148. Angew. Chem. 1998, 110, 3061.
149. Hildebrand, J. P.; Marsden, S. P. Synlett 1996, 893.
150. Charette, A. B.; Pereira De Freitas-Gil, R. Tetrahedron Lett. 1997, 38, 2809.
151. Desurmont, G.; Klein, R.; Uhlenbrock, S.; Laloë, E.; Deloux, L.; Giolando, D. M.; Kim, Y. W.; Pereira, S.; Srebnik, M. Organometallics 1996, 15, 3323.
152. Desurmont, G.; Dalton, S.; Giolando, D. M.; Srebnik, M. J. Org. Chem. 1997, 62, 8907.
153. Hollis, W. G. Jr.; Lappenbusch, W. C.; Everberg, K. A.; Woleben, C. M. Tetrahedron Lett. 1993, 34, 7517.
154. Thormeier, S.; Carboni, B.; Kaufmann, D. E. J. Organomet. Chem. 2002, 657, 136.