Enantiospecific synthesis of heterocycles from α-amino acids

Chemical Reviews

Volumn 96, Issue 6, 1996, Pages 1825-1872

  Sardina, F Javier ^a   Rapoport, Henry ^b  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 8344249465     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr9300348     Document Type: Article

References (305)

1. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1983-1984; 5 volumes.
2. (a) Coppola, G. M.; Schuster, H. F. Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids; Wiley: New York, 1987.
3. (b) Hanessian, S. Total Synthesis of Natural Products: The 'Chiron' Approach; Pergamon: Oxford, 1983.
4. (c) Scott, J. W. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic: New York, 1984; Vol. 4, pp 1-226.
5. Methoden der Organischen Chemie (Houben-Weil); Müller, E., Wünsch, E., Eds.; Georg Thieme Verlag: Stuttgart, 1974; Vol. 15, parts 1 and 2.
6. Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149-164.
7. Schurig, V.; Nowotny, A. P. Angew. Chem., Int. Ed. Engl. 1990, 29, 939-957.
8. (a) Allenmark, S. G. Chromatographic Enantioseparation. Methods and Applications; Ellis Horwood Ltd.: Chichester, 1988.
9. (b) Pirkle, W. H.; Pochapsky, T. C. Adv. Chromatogr. (N. Y.) 1987, 29, 939-957.
10. (a) Parker, D. Chem. Rev. 1991, 91, 1441-1457.
11. (b) Gupta, A. K.; Kazlauskas, R. J. Tetrahedron: Asymmetry 1992, 3, 243-246.
12. The use of the term enantiomeric ratio for the description of the enantiomeric purity of a compound has been advocated (in a preliminary form) by a working party on stereochemical terminology (IUPAC): Halevi, E. A. Chem. Eng. News 1992, 70 (43), 2.
13. For an enlightening discussion of the pitfalls of chiroptical methods for the determination of enantiomeric purity see ref 7a.
14. Baker, W. R.; Condon, S. L.; Spanton, S. Tetrahedron Lett. 1992, 33, 1573-1576.
15. Baker, W. R.; Condon, S. L. Tetrahedron Lett. 1992, 33, 1577-1580.
16. Caplar, V.; Lisini, A.; Kajfez, F.; Kolbah, D.; Sunjic, V. J. Org. Chem. 1978, 43, 1355-1360.
17. Berry, M. B.; Craig, D. Synlett 1992, 41-44.
18. Eguchi, S.; Yamashita, K.; Matsushita, Y. Synlett 1992, 295-296.
19. (a) Jouin, P.; Castro, B.; Nisato, D. J. Chem. Soc., Perkin Trans. 1 1987, 1177-1182.
20. (b) Wittenberger, S. J.; Baker, W. R.; Donner, B. G.; Hutchins, C. W. Tetrahedron Lett. 1991, 32, 7655-7658.
21. (a) Maibaum, J.; Rich, D. H. J. Med. Chem. 1989, 32, 1571-1576.
22. (b) Jiang, J.; Li, W.-R.; Przeslawski, R. M.; Joullié, M. M. Tetrahedron Lett. 1993, 34, 6705-6708.
23. Midland, M. M.; Afonso, M. M. J. Am. Chem. Soc. 1989, 111, 4368-4371.
24. Waldmann, H.; Braun, M. J. Org. Chem. 1992, 57, 4444-4451.
25. (b) Waldmann, H.; Braun, M.; Dräger, M. Angew. Chem., Int. Ed. Engl. 1990, 29, 1468-1471.
26. (c) Waldmann, H. Angew. Chem., Int. Ed. Engl. 1988, 27, 274-275.
27. (d) Waldmann, H.; Braun, M.; Weymann, M.; Gewehr, M. Synlett 1991, 881-884.
28. (e) Waldmann, H.; Braun, M.; Dräger, M. Tetrahedron: Asymmetry 1991, 2, 1231-1246.
29. For closely related asymmetric hetero-Diels-Alder approaches to chiral piperidines, azabicyclo-[2.2.1]heptanes and azabicyclo[2.2.2]octanes, see: (f) Waldmann, H.; Braun, Gazz. Chim. Ital. 1991, 121, 277-284. (g) Waldmann, H. Liebigs Ann. Chem. 1989, 231-238. (h) Grieco, P. A.; Bahsas, A. J. Org. Chem. 1987, 52, 5746-5749. (i) For a possible application to the synthesis of (-)-porantheridine, see: Commins, D. L.; Hong, H. J. Am. Chem. Soc. 1993, 115, 8851-8852.
30. For closely related asymmetric hetero-Diels-Alder approaches to chiral piperidines, azabicyclo-[2.2.1]heptanes and azabicyclo[2.2.2]octanes, see: (f) Waldmann, H.; Braun, Gazz. Chim. Ital. 1991, 121, 277-284. (g) Waldmann, H. Liebigs Ann. Chem. 1989, 231-238. (h) Grieco, P. A.; Bahsas, A. J. Org. Chem. 1987, 52, 5746-5749. (i) For a possible application to the synthesis of (-)-porantheridine, see: Commins, D. L.; Hong, H. J. Am. Chem. Soc. 1993, 115, 8851-8852.
31. For closely related asymmetric hetero-Diels-Alder approaches to chiral piperidines, azabicyclo-[2.2.1]heptanes and azabicyclo[2.2.2]octanes, see: (f) Waldmann, H.; Braun, Gazz. Chim. Ital. 1991, 121, 277-284. (g) Waldmann, H. Liebigs Ann. Chem. 1989, 231-238. (h) Grieco, P. A.; Bahsas, A. J. Org. Chem. 1987, 52, 5746-5749. (i) For a possible application to the synthesis of (-)-porantheridine, see: Commins, D. L.; Hong, H. J. Am. Chem. Soc. 1993, 115, 8851-8852.
32. For closely related asymmetric hetero-Diels-Alder approaches to chiral piperidines, azabicyclo-[2.2.1]heptanes and azabicyclo[2.2.2]octanes, see: (f) Waldmann, H.; Braun, Gazz. Chim. Ital. 1991, 121, 277-284. (g) Waldmann, H. Liebigs Ann. Chem. 1989, 231-238. (h) Grieco, P. A.; Bahsas, A. J. Org. Chem. 1987, 52, 5746-5749. (i) For a possible application to the synthesis of (-)-porantheridine, see: Commins, D. L.; Hong, H. J. Am. Chem. Soc. 1993, 115, 8851-8852.
33. Gómez-Monterrey, I.; Dominguez, M. J.; González-Muñiz, R.; Harto, J. R.; García-López, M. T. Tetrahedron Lett. 1991, 32, 3563-3564.
34. Lubell, W. D.; Rapoport, H. J. Am. Chem. Soc. 1988, 110, 1447-1455 and references therein.
35. Martín-Martínez, M.; García-López, M. T.; González-Muñiz, R. Tetrahedron Lett. 1992, 33, 2187-2190.
36. Cooper, J.; Knight, D.; Gallagher, P. T. W. J. Chem. Soc., Perkin Trans, 1 1991, 705-713.
37. (a) Wang, C.-L.; Calabrese, J. C. J. Org. Chem. 1991, 56, 4341-4343.
38. (b) Iida, H.; Yamazaki, N.; Kibayashi, C. J. Org. Chem. 1987, 52, 1956-1962.
39. (a) Takahata, H.; Bandoh, H.; Momose, T. J. Org. Chem. 1992, 57, 4401-4404.
40. (b) Takahata, H.; Bandoh, H.; Momose, T. Tetrahedron: Asymmetry 1991, 2, 351-352.
41. (c) Takahata, H.; Takehara, H.; Ohkubo, N.; Momose, T. Tetrahedron: Asymmetry 1990, 1, 561-566.
42. (d) Arseniyadis, S.; Huang, P. Q.; Husson, H.-P. Tetrahedron Lett. 1988, 29, 1391-1394.
43. (a) Takahata, H.; Bandoh, H.; Hanayama, M.; Momose, T. Tetrahedron: Asymmetry 1992, 3, 607-608.
44. (b) Dolle, R. E.; Osifo, K. I.; Li, C.-S. Tetrahedron Lett. 1991, 32, 5029-5030.
45. (c) For a longer (18 steps) enantiodivergent synthesis of (+)- and (-)-pinidine from L-tartaric acid see ref 36d.
46. (a) Jurczak, J.; Golebiowski, A.; Raczko, J. Tetrahedron Lett. 1988, 29, 5975-5978.
47. (b) Golebiowski, A.; Jacobsson, U.; Raczko, J.; Jurczak, J. J. Org. Chem. 1989, 54, 3759-3760.
48. Jurczak, J.; Golebiowski, A.; Raczko, J. J. Org. Chem. 1989, 54, 2495-2496.
49. (a) Hamada, Y.; Kawai, A.; Kohno, Y.; Hara, O.; Shioiri, T. J. Am. Chem. Soc. 1989, 111, 1524-1525.
50. (b) Hamada, Y.; Hara, O.; Kawai, A.; Kohno, Y.; Shioiri, T. Tetrahedron 1991,47, 8635-8652.
51. Broady, S. D.; Rexhausen, J. E.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1991, 708-710.
52. Ward, R. A.; Procter, G. Tetrahedron Lett. 1992, 33, 3359-3362.
53. Prasad, J. V. N. V.; Rich, D. H. Tetrahedron Lett. 1991, 32, 5857-5860.
54. Evans, P. A.; Holmes, A. B.; Russel, K. Tetrahedron: Asymmetry 1990, 1, 593-596.
55. Anslow, A. S.; Harwood, L. M.; Phillips, H.; Watkin, D. Tetrahedron: Asymmetry 1991, 2, 997-1000.
56. (a) Jegham, S.; Das, B. C. Tetrahedron Lett. 1989, 30, 2801-2804.
57. (b) Hunag, P. Q.; Arseniyadis, S.; Husson, J.-P. Tetrahedron Lett. 1987, 28, 547-550.
58. Jegham, S.; Fourrey, J.-L.; Das, B. C. Tetrahedron Lett. 1989, 30, 1959-1962.
59. (a) Jefford, C. W.; Tang, Q.; Zaslona, A. J. Am. Chem. Soc. 1991, 113, 3513-3518.
60. (b) Yamazaki, N.; Kibayashi, C. Tetrahedron Lett. 1988, 29, 5767-5768.
61. (c) Ito, M.; Kibayashi, C. Tetrahedron Lett. 1990, 31, 5065-5068.
62. (d) Yamazaki, N.; Kibayashi, C. J. Am. Chem. Soc. 1989, 111, 1396-1408.
63. (e) Momose, T.; Toyooka, N.; Seki, S.; Hirai, Y. Chem. Pharm. Bull. 1990, 38, 2072-2074.
64. Williams, R. M.; Brunner, E. J.; Sabol, M. R. Synthesis 1988, 963-966.
65. Martens, J.; Seheunemann, M. Tetrahedron Lett. 1991, 32, 1417-1418.
66. Plata, D. J.; Leanna, M. R.; Morton, H. E. Tetrahedron Lett. 1991, 32, 3623-3626 and references therein.
67. Saito, H.; Hirata, T. Tetrahedron Lett. 1987, 28, 4065-4068.
68. (a) Jegham, S.; Das, B. C. Tetrahedron Lett. 1988, 29, 4419-4422.
69. (b) Meyer, A. I.; Dupre, B. Heterocycles 1987, 25, 113-116.
70. Shono, T.; Kise, N. Chem. Lett. 1987, 697-700.
71. (a) Boger, D. L.; Yohannes, D.; Myers, J. B., Jr. J. Org. Chem. 1992, 57, 1319-1321.
72. (b) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429.
73. (c) Inaba, T.; Umezawa, I.; Yuasa, M.; Inoue, T.; Mihashi, S.; Itokawa, H.; Ogura, K. J. Org. Chem. 1987, 52, 2957-2958.
74. (d) Nishiyama, S.; Suzuki, Y.; Yamamura, S. Tetrahedron Lett. 1988, 29, 559-562.
75. (a) Bailey, P. D.; Hollinshead, S. P.; McLay, N. R. Tetrahedron Lett. 1987, 28, 5177-5180.
76. (b) Bailey, P. D. Tetrahedron Lett. 1987, 28, 5181-5184.
77. Zang, L.-H.; Cook, J. M. Heterocycles 1988, 27, 1357-1363.
78. O'Malley, G. J.; Cava, M. P. Tetrahedron Lett. 1987, 28, 1131-1134.
79. Huizenga, R. H.; Pandit, U. K. Tetrahedron 1992, 48, 6521-6528.
80. (a) Zhang, L. H.; Cook, J. M. J. Am. Chem. Soc. 1990, 112, 4088-4090.
81. (b) Zang, L.-H.; Cook, J. M. Heterocycles 1988, 27, 2795-2802.
82. (a) Magnus, P.; Mugrage, B.; DeLuca, M. R.; Cain, G. A. J. Am. Chem. Soc. 1990, 112, 5220-5230.
83. (b) Magnus, P.; Mugrage, B.; DeLuca, M.; Cain, G. A. J. Am. Chem. Soc. 1989, 111, 786-789.
84. Bailey, P. D.; McLay, N. R. Tetrahedron Lett. 1991, 32, 3895-3898.
85. (a) Bourne, G. T.; Crich, D.; Davies, J. W.; Horwell, D. C. J. Chem. Soc., Perkin Trans. 1 1991, 1693-1699.
86. (b) Crich, D.; Davies, J. W. J. Chem. Soc., Chem. Commun. 1989, 1418-1419.
87. (a) Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1991, 47, 155-172.
88. (b) Baldwin, J. E.; Moloney, M. G.; Parsons, A. F. Tetrahedron 1990, 46, 7263-7282.
89. (c) Baldwin, J. E.; Li, C.-S. J. Chem. Soc.. Chem. Commun. 1987, 166-168.
90. Baldwin, J. E.; Turner, S. C. M.; Moloney, M. G. Tetrahedron Lett. 1992, 33, 1517-1520.
91. (a) Barco, A.; Benetti, S.; Pollini, G. P.; Spalluto, G.; Zanirato, V. J. Chem. Soc., Chem. Commun. 1991, 390-391.
92. (b) Barco, A.; Benetti, S.; Casolari, A.; Pollini, G. P.; Spalluto, G. Tetrahedron Lett. 1990, 31, 4917-4920.
93. (a) Golebiowski, A.; Kozak, J.; Jurczak, J. J. Org. Chem. 1991, 56, 7344-7347.
94. (b) Golebiowski, A.; Kozak, J.; Jurczak, J. Tetrahedron Lett. 1989, 30, 7103-7104.
95. (c) Golebiowski, A.; Jurczak, J. J. Chem. Soc., Chem. Commun. 1989, 263-264.
96. (a) Palomo, C.; Cossío, F. P.; Cuevas, C.; Odriozola, J. M.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4827-4830.
97. (b) Palomo, C.; Cossío, F. P.; Cuevas, C. Tetrahedron Lett. 1991, 32, 3109-3110.
98. (c) Palomo, C.; Cossío, F. P.; Cuevas, C.; Lecea, B.; Mielgo, A.; Roman, P.; Luque, A.; Martínez-Ripoll, M. J. Am Chem. Soc. 1992, 114, 9360-9369.
99. Bailey, S. W.; Chandrasekaran, R. Y.; Ayling, J. E. J. Org. Chem. 1992, 57, 4470-4477.
100. Galéotti, N.; Montagne, C.; Pancet, C.; Jouin, P. Tetrahedron Lett. 1992, 33, 2807-2810.
101. (a) Wipf, P.; Miller, C. P. Tetrahedron Lett. 1992, 33, 907-910.
102. (b) Wipf, P.; Miller, C. P. J. Am. Chem. Soc. 1992, 114, 10975-10977.
103. Jackson, R. F. W.; Wood, A.; Wythes, M. J. Synlett 1990, 735-736.
104. Roush, W. R.; Brown, B. B. J. Org. Chem. 1992, 57, 3380-3387.
105. (a) Smith, A. B., III; Leahy, J. W.; Noda, I.; Remiszewski, S. W.; Liverton, N. J.; Zibuck, R. J. Am. Chem. Soc. 1992, 114, 2995-3007.
106. (b) Smith, A. B., III; Noda, I.; Remiszewski, S. W.; Liverton, N. J.; Zibuck, R. J. Org. Chem. 1990, 55, 3977-3979.
107. (c) Zibuck, R.; Liverton, N. J.; Smith, A. B., III J. Am. Chem. Soc. 1986, 108, 2451-2453.
108. White, J. D.; Kawasaki, M. J. Am. Chem. Soc. 1990, 112, 4991-4993.
109. Beagley, B.; Betts, M. J.; Pritchard, R. G.; Schofield, A.; Stoodley, R. J.; Vohra, S. J. Chem, Soc., Chem. Commun. 1991, 924-925.
110. Jones, R. J.; Rapoport, H. J. Org. Chem. 1990, 55, 1144-1146.
111. Yamanoi, K.; Ohfune, Y.; Watanabe, K.; Li, P. N.; Takeuchi, H. Tetrahedron Lett. 1988, 29, 1181-1184.
112. Compagnone, R. S.; Rapoport, H. J. Org. Chem. 1986, 51, 1713-1719.
113. Shono, T.; Matsumura, Y.; Tsubata, K.; Uchida, K. J. Org. Chem. 1986, 51, 2590-2592.
114. (a) Shono, T.; Matsumura, Y.; Onomura, O.; Yamada, Y. Tetrahedron Lett. 1987, 28, 4073-4074.
115. (b) Matsumune, M.; Ogawa, M. Heterocycles 1980, 14, 169-173.
116. (c) Matsumune, M.; Ogawa, M. Heterocycles 1979, 12, 159.
117. (d) For an alternative enantiospecific synthesis of carpaine and azimine from D-glucose, see: Hanessian, S.; Frenette, R. Tetrahedron Lett. 1979, 3391-3394.
118. (a) González-Muñiz, R.; Domínguez, M. J.; García-López, M. T. Tetrahedron 1992, 48, 5191-5198.
119. (b) Gómez-Monterrey, I.; Domínguez, M. J.; González-Muñiz, R.; Harto, J. R.; García-López, M. T. Tetrahedron Lett. 1991, 32, 1089-1092.
120. (a) Boeckman, R. K., Jr.; Weidner, C. H.; Perni, R. B.; Napier, J. J. J. Am. Chem. Soc. 1989, 111, 8036-8037.
121. (b) Paquette, L. A.; Macdonald, D.; Anderson, L. G.; Wright, J. J. Am. Chem. Soc. 1989, 111, 8037-8039.
122. (a) Sauerberg, P.; Chen, J.; WoldeMussie, E.; Rapoport, H. J. Med. Chem. 1989, 32, 1322-1326.
123. (b) Kim, T. H.; Rapoport, H. J. Org. Chem. 1990, 55, 3699-3702.
124. Frick, J. A.; Klassen, J. B.; Bathe, A.; Abramson, J. M.; Rapoport, H. Synthesis 1992, 621-623.
125. Hoffmann, M. G.; Zeiss, H.-J. Tetrahedron Lett. 1992, 33, 2669-2672.
126. Bold, G.; Steiner, H.; Moesch, L.; Walliser, B. Helv. Chim. Acta 1990, 73, 405-410.
127. (a) Choi, J.-R.; Han, S.; Cha, J. K.; Tetrahedron Lett. 1991, 32, 6469-6472.
128. (b) Takahata, H.; Banba, Y.; Momose, T. Tetrahedron; Asymmetry 1990, 1, 763-764.
129. Wolf, J.-P.; Rapoport, H. J. Org. Chem. 1989, 54, 3164-3173.
130. Garvey, D. S.; May, P. D.; Nadzan, A. M. J. Org. Chem. 1990, 55, 936-940.
131. (a) Feldman, P. L.; Rapoport, H. J. Am. Chem. Soc. 1987, 109, 1603-1604.
132. (b) Feldman, P. L.; Rapoport, H. J. Org. Chem. 1986, 51, 3882-3890.
133. Gmeiner, P.; Feldman, P. L.; Chu-Moyer, M. Y.; Rapoport, H. J. Org. Chem. 1990, 55, 3068-3074.
134. (a) McGarvey, G. J.; Williams, J. M.; Hiner, R. N.; Matsubara, Y.; Oh, T. J. Am. Chem. Soc. 1986, 108, 4943-4952.
135. (b) McGarvey, G. J.; Hiner, R. N.; Williams, J. M.; Matsubara, Y.; Poarch, J. W. J. Org. Chem. 1986, 51, 3742-3744.
136. (c) Overly, K. R.; Williams, J. M.; McGarvey, G. J. Tetrahedron Lett. 1990, 31, 4573-4576.
137. McGarvey, G. J.; Wilson, K. J.; Shanholtz, C. E. Tetrahedron Lett. 1992, 33, 2641-2644.
138. (a) Ojima, I.; Shimizu, N.; Qiu, X.; Chen, H.-J. C.; Nakahashi, K. Bull. Soc. Chim. Fr. 1987, 649-658.
139. (b) Manhas, M. S.; Wagle, D. R.; Chiang, J.; Bose, A. K. Heterocycles 1988, 27, 1755-1802.
140. (a) Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Schofield, C. J. Tetrahedron 1991, 47, 5835-5840.
141. (b) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Schofield, C. J. J. Chem. Soc., Chem. Commun. 1990, 720-721.
142. (c) Baldwin, J. E.; Adlington, R. M.; Gollins, D. W.; Schofield, C. J. Tetrahedron 1990, 46, 4733-4748.
143. Hanessian, S.; Sumi, K.; Vanasse, B. Synlett 1992, 33-34.
144. Thomas, E. J.; Williams, A. C. J. Chem. Soc., Chern. Commun. 1987, 992-994.
145. (a) Konopelski, J. P.; Chu, K. S.; Negrete, G. R. J. Org. Chem. 1991, 56, 1355-1357.
146. (b) Chu, K. S.; Negrete, G. R.; Konopelski, J. P. J. Org. Chem. 1991, 56, 5196-5202.
147. (c) Chu, K. S.; Negrete, G. R.; Konopelski, J. P.; Lakner, F. J.; Woo, N.-T.; Olmstead, M. N. J. Am. Chem. Soc. 1992, 114, 1800-1812.
148. (a) Kurzmeier, H.; Schmidtchen, F. P. J. Org. Chem. 1990, 55, 3749-3755.
149. (b) Schmidtchen, F. P. Tetrahedron Lett. 1990, 31, 2269-2272.
150. (c) Gleich, A.; Schmidtchen, F. P. Chem. Ber. 1990, 123, 907-915.
151. (a) Galán, A.; Andreu, D.; Echavarren, A. M.; Prados, P.; Mendoza, J. J. Am. Chem. Soc. 1992, 114, 1511-1512.
152. (b) Echavarren, A.; Galán, A.; Mendoza, J.; Salmerón, A.; Lehn, J.-M. Helv. Chim. Acta 1988, 71, 685-693.
153. Thottathil, J. K.; Moniot, J. L.; Mueller, R. H.; Wong, M. K. Y.; Kissick, T. P. J. Org. Chem. 1986, 57, 3140-3143.
154. (a) Armstrong, R. W.; DeMattei, J. A. Tetrahedron Lett. 1991, 32, 5749-5752.
155. (b) Baldwin, J. E.; Moloney, M. G.; Shim, S. B. Tetrahedron Lett. 1991, 32, 1379-1380.
156. Hon, Y.-S.; Chang, Y.-C.; Gong, M.-L. Heterocycles, 1990, 31, 191-195.
157. Baldwin, J. E.; Miranda, T.; Moloney, M.; Hokelek, T. Tetrahedron 1989, 45, 7459-7468.
158. Dikshit, D. K.; Panday, S. K. J. Org. Chem. 1992, 57, 1920-1924.
159. Avent, A. G.; Bowler, A. N.; Doyle, P. M.; Marchand, C. M.; Young, D. W. Tetrahedron Lett. 1992, 33, 1509-1512.
160. Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 1859-1866.
161. (a) Yoda, H.; Naito, S.; Takabe, K.; Tanaka, N.; Hosoya, K. Tetrahedron Lett. 1990, 31, 7623-7626.
162. (b) Rehnberg, N.; Magnusson, G. Tetrahedron Lett. 1988, 29, 3599-3602.
163. Yanagida, M.; Hashimoto, K.; Ishida, M.; Shinozaki, H.; Shirahama, H. Tetrahedron Lett. 1989, 30, 3799-3802.
164. Shimamoto, K.; Ohfune, Y. Tetrahedron Lett. 1989, 30, 3803-3804.
165. (a) Langlois, N.; Andriamialisoa, R. Z. Tetrahedron Lett. 1991, 32, 3057-3058.
166. (b) For a related 1,4-addition of an stabilized carbanion see ref 92b.
167. Somfai, P.; He, H. M.; Tanner, D. Tetrahedron Lett. 1991, 32, 283-286.
168. (a) Hanessian, S.; Ratovelomanana, V. Synlett 1990, 501-503.
169. (b) Hanessian, S.; Ratovelomanana, V. Synlett 1991, 222-224.
170. (a) Ikota, N.; Hanaki, A. Chem. Pharm. Bull. 1987, 35, 2140-2143.
171. (b) Ikota, N.; Hanaki, A. Heterocycles 1987, 26, 2369-2370.
172. (c) Ikota, N.; Hanaki, A. Heterocycles 1988, 27, 2535-2537.
173. (a) Miller, S. A.; Chamberlin, A. R. J. Am. Chem. Soc. 1990, 112, 8100-8112 and references therein,
174. (b) Benet, R. B., III; Choi, J.-R.; Montgomery, W. D.; Cha, J. K. J. Am. Chem. Soc. 1989, 111, 2580-2582 and references therein,
175. (c) Carpenter, N. M.; Fleet, G. W. J.; de Bello, I. C.; Winchester, B.; Fellows, L. E.; Nash, R. J. Tetrahedron Lett. 1989, 30, 7261-7264 and references therein,
176. (d) Denner, J. M.; Hart, D. J.; Ramesh, S. J. Org. Chem. 1988, 53, 6022-6030.
177. (e) Adams, C. E.; Walker, F. J.; Sharpless, K. B. J. Org. Chem. 1985, 50, 420-422.
178. (a) Rüeger, H.; Benn, M. Heterocycles 1982, 19, 23-25.
179. (b) Niwa, H.; Okamoto, O.; Miyachi, Y.; Uosaki, Y.; Yamada, K. J. Org. Chem. 1987, 52, 2941-2943.
180. (c) Hamada, Y.; Tanada, Y.; Yokokawa, F.; Shioiri, T. Tetrahedron Lett. 1991, 32, 5983-5986.
181. Ikota, N. Tetrahedron Lett. 1992, 33, 2553-2556.
182. (a) Ikota, N. Heterocycles 1989, 29, 1469-1472.
183. (b) For leading references see: Anzeveno, P. B.; Creemer, L. J. Tetrahedron Lett. 1990, 31, 2085-2088.
184. (a) Howard, M. H.; Sardina, F. J.; Rapoport, H. J. Org. Chem. 1990, 55, 2829-2838.
185. (b) Sardina, F. J.; Howard, M. H.; Koskinen, A. M. P.; Rapoport, H. J. Org. Chem. 1989, 54, 4654-4660.
186. Sardina, F. J.; Howard, M. H.; Morningstar, M.; Rapoport, H. J. Org. Chem. 1990, 55, 5025-5033.
187. Koskinen, A. M. P.; Ghiaci, M. Tetrahedron Lett. 1990, 31, 3209-3212.
188. (a) Fang, F. G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 30, 3621-3624.
189. (b) Fang, F. G.; Prato, M.; Kim, G.; Danishefsky, S. J. Tetrahedron Lett. 1989, 30, 3625-3628.
190. Jain, S.; Sujatha, K.; Krishna, K. V. R.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988.
191. (a) Saliou, C.; Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron Lett. 1991, 32, 3365-3368.
192. (b) Provot, O.; Célérier, J. P.; Petit, H.; Lhommet, G. J. Org. Chem. 1992, 57, 2163-2166.
193. Rosset, S.; Célérier, J. P.; Lhommet, G. Tetrahedron Lett. 1991, 32, 7521-7524.
194. (a) Ohta, T.; Hosoi, A.; Kimura, T.; Nozoe, S. Chem. Lett. 1987, 2091-2094.
195. (b) Ohta, T.; Hosoi, A.; Nozoe, S. Tetrahedron Lett. 1988, 29, 329-332.
196. Ohta, T.; Sato, N.; Kimura, T.; Nozoe, S. Tetrahedron Lett. 1988, 29, 4305-4308.
197. (a) Pearson, W. H.; Bergmeier, S. C.; Williams, J. P. J. Org. Chem. 1992, 57, 3977-3987.
198. (b) Pearson, W. H.; Bergmeier, S. C. J. Org. Chem. 1991, 56, 1976-1978.
199. (c) Heidt, P. C.; Bergmeier, S. C.; Pearson, W. H. Tetrahedron Lett. 1990, 31, 5441-5444.
200. Chida, N.; Tobe, T.; Okada, S.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1992, 1064-1066.
201. Bailey, P. D.; Bryans, J. S. Tetrahedron Lett. 1988, 29, 2231-2234.
202. Bolós, J.; Pérez, A.; Gubert, S.; Anglada, L.: Sacristán, A.; Ortiz, J. A. J. Org. Chem. 1992, 57, 3535-3539.
203. (a) Kotsuki, H.; Kusumi, T.; Inoue, M.; Ushio, Y.; Ochi, M. Tetrahedron Lett. 1991, 32, 4159-4162.
204. (b) Taber, D. F.; Deker, P. B.; Fales, H. M.; Jones, T. H.; Lloyd, H. A. J. Org. Chem. 1988, 53, 2968-2971.
205. Fleurant, A.; Célérier, J. P.; Lhommet, G. Tetrahedron.: Asymmetry 1992, 3, 695-696.
206. Taschner, M. J.; Huang, Y.; El-Alali, A.; Chen, L.; Youngs, W. J. Tetrahedron Lett. 1992, 33, 2765-2768.
207. (a) Figadère, B.; Harmange, J. C.; Laurens, A.; Cavé A. Tetrahedron Lett. 1991, 32, 7539-7542.
208. For the preparation of a related γ-butyrolactone, see: (b) Harmange, J.-C.; Figadère, B.; Hocquemiller, R. Tetrahedron: Asymmetry 1991, 2, 347-350.
209. (a) Keusenkothen, P. F.; Smith, M. B. Tetrahedron 1992, 48, 2977-2992.
210. (b) Keusenkothen, P. F.; Smith, M. B. Tetrahedron Lett. 1989, 30, 3369-3372.
211. Smith, A. L.; Williams, S. F.; Holmes, A. B.; Hughes, L. R.; Lidert, Z.; Swithenbank, C. J. Am. Chem. Soc. 1988, 110, 8696-8698.
212. Evans, D. A.; Lundy, K. M. J. Am. Chem. Soc. 1992, 114, 1495-1496.
213. Lessen, T. A.; Demko, D. M.; Weinreb, S. M. Tetrahedron Lett. 1990, 31, 2105-2108.
214. Fukuyama, T.; Lin, S.-C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050-7051.
215. Fukuyama, T. In Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; Jai Press: Greenwich, 1992; Vol. 2, pp 241-247.
216. (a) Mori, S.; Ohno, T.; Harada, H.; Aoyama, T.; Shioiri, T. Tetrahedron 1991, 47, 5051-5070.
217. (b) Mori, S.; Aoyama, T.; Shioiri, T. Tetrahedron Lett. 1986, 27, 6111-6114.
218. Nagasaka, T.; Koseki, Y.; Hamaguchi, F. Tetrahedron Lett. 1989, 30, 1871-1872.
219. (a) Wistrand, L.-G.; Skrinjar, M. Tetrahedron 1991, 47, 573-582.
220. (b) Skrinjar, M.; Wistrand, L. G. Tetrahedron Lett. 1990, 31, 1775-1778.
221. Asada, S.; Kato, M.; Asai, K.; Ineyama, T.; Nishi, S.; Izawa, K.; Shono, T. J. Chem. Soc., Chem. Commun. 1989, 486-488.
222. (a) Moeller, K. D.; Rothfus, S. L. Tetrahedron Lett. 1992, 33, 2913-2916.
223. (b) Moeller, K. D.; Rothfus, S. L.; Wong, P. L. Tetrahedron 1991, 47, 583-592.
224. Jolly, R. S.; Livinghouse T. J. Am. Chem. Soc. 1988, 110, 7536-7538.
225. Seijas, J. A.; Vázquez-Tato, M. P.; Castedo, L.; Estévez, R. J.; Onega, M. G.; Ruiz, M. Tetrahedron 1992, 48, 1637-1642.
226. Beckett, R. P.; Davies, S. G.; Mortlock, A. A. Tetrahedron: Asymmetry 1992, 3, 123-136.
227. (a) Knight, D. W.; Share, A. C.; Gallagher, P. T. J. Chem. Soc., Perkin Trans. 1 1991, 1615-1616.
228. (b) Nagao, Y.; Dai, W.-M.; Ochiai, M.; Tsukagoshi, S.; Fujita, E. J. Am. Chem. Soc. 1988, 110, 289-291.
229. (a) Overman, L. E.; Robinson, L. A.; Zablocki, J. J. Am. Chem. Soc. 1992, 114, 368-369.
230. (b) Lett, R. M.; Overman, L. E.; Zablocki, J. Tetrahedron Lett. 1988, 29, 6541-6544.
231. Goldstein, S. W.; Overman, L. E.; Rabinowitz, M. H. J. Org. Chem. 1992, 57, 1179-1190.
232. Trost, B. M.; Scanlan, T. S. J. Am. Chem. Soc. 1989, 111, 4988-4990.
233. (a) St-Denis, Y.; Chan, T.-H. J. Org. Chem. 1992, 57, 3078-3085.
234. (b) Gerspacher, M.; Rapoport, H. J. Org. Chem. 1991, 56, 3700-3706.
235. (c) Fleet, G. W. J.; Ramsden, N. G.; Molyneux, R. J.; Jacob, G. S. Tetrahedron Lett. 1988, 29, 3603-3606.
236. (d) Hamana, H.; Ikota, N.; Ganem, B. J. Org. Chem. 1987, 52, 5492-5494.
237. (a) Williams, R. M.; Glinka, T.; Kwast, E. J. Am. Chem. Soc. 1988, 110, 5927-5929.
238. (b) Seebach, D.; Boes, M.; Naef, R.; Schweizer, W. F. J. Am. Chem. Soc. 1983, 105, 5390-5398.
239. (a) Thottathil, J. K.; Moniot, J. L. Tetrahedron Lett. 1986, 27, 151-154.
240. (b) Kronenthal, D. R.; Mueller, R. H.; Kuester, P. L.; Kissick, T. P.; Johnson, E. J. Tetrahedron Lett. 1990, 37,1241-1244.
241. (c) Hudlicky, M.; Merola, J. S. Tetrahedron Lett. 1990, 31, 7403-7406.
242. (c) Manfré, F.; Kern, J.-M.; Biellmann, J.-F. J. Org. Chem. 1992, 57, 2060-2065.
243. (a) Sibi, M. P.; Christensen, J. W. Tetrahedron Lett. 1990, 31, 5689-5692.
244. (b) Sibi, M. P.; Christensen, J. W.; Li, B.; Renhowe, P. A. J. Org. Chem. 1992, 57, 4329-4330.
245. (c) Knight, D. W.; Sibley, A. W. Tetrahedron Lett. 1993, 34, 6607-6610.
246. Bhide, R.; Mortezaei, R.; Scilimati, A.; Sih, C. J. Tetrahedron Lett. 1990, 37, 4827-4830.
247. Barret, A. G. M.; Pilipauskas, D. J. Org. Chem. 1991, 56, 2787-2800.
248. (a) Remuzon, P.; Bouzard, D.; Guiol, C.; Jacquet, J.-P. J. Med. Chem. 1992, 35, 2898-2909.
249. (b) Braish, T. F.; Fox, D. E. J. Org. Chem. 1990, 55, 1684-1687.
250. (c) Jordis, U.; Sauter, F.; Siddiqi, S. M.; Küenburg, B.; Bhattacharya, K. Synthesis 1990, 925-930.
251. Jordis, U.; Sauter, F.; Siddiqi, S. M. Indian J. Chem. 1989, 28B, 294-296.
252. Smith, A. B., III; Holcomb, R. C.; Guzman, M. C.; Keenan, T. P.; Sprengeler, P. A.; Hirschmann, R. Tetrahedron Lett. 1993, 34, 63-66.
253. Franciotti, M.; Mann, A.; Mordini, A.; Taddei, M. Tetrahedron Lett. 1993, 34, 1355-1358.
254. Plummer, J. S.; Emery, L. A.; Stier, M. A.; Suto, M. J. Tetrahedron Lett. 1993, 34, 7529-7532.
255. (a) Angle, S. R.; Breitenbucher, J. G.; Arnaiz, D. O. J. Org. Chem. 1992, 57, 5947-5955.
256. (b) Angle, S. R.; Breitenbucher, J. G. Tetrahedron Lett. 1993, 34, 3985-3988.
257. (a) Baldwin, J. E.; Hulme, C.; Edwards, A. J.; Schofield, C. J.; Parkes, K. E. B. Tetrahedron Lett. 1993, 34, 1665-1668.
258. (b) Baldwin, J. E.; Hulme, C.; Schofield, C. J.; Edwards, A. J. J. Chem. Soc., Chem. Commun. 1993, 935-936.
259. Takahata, H.; Inose, K.; Momose, T. Heterocycles 1994, 38, 269-271.
260. Boger, D. L.; Yohannes, D.; Zhou, J.; Patane, M. A. J. Am. Chem. Soc. 1993, 115, 3420-3430.
261. Abell, A. D.; Taylor, J. M. J. Org. Chem. 1993, 58, 14-15.
262. Wipf, P.; Kim, Y. J. Org. Chem. 1993, 58, 1649-1650.
263. (a) Tomioka, K.; Kubota, Y.; Koga, K. Tetrahedron 1993, 49, 1891-1900.
264. (b) For a related approach to azasteganes, see: Kubota, Y.; Kawasaki, H.; Tomioka, K.; Koga, K. Tetrahedron 1993, 49, 3081-3090.
265. Erickson, S. D.; Simon, J. A.; Still, W. C. J. Org. Chem. 1993, 58, 1305-1308.
266. McGrane, P. L.; Livinghouse, T. J. Am. Chem. Soc. 1993, 115, 11485-11489.
267. Bailey, P. D.; Hollinshead, S. P.; McLay, N. R.; Morgan, K.; Palmer, S. J.; Prince, S. N.; Reynolds, C. D.; Wood, S. D. J. Chem. Soc., Perkin Trans, 1 1993, 431-439.
268. (a) Bailey, P. D.; Hollinshead, S. P.; McLay, N. R.; Everett, J. H.; Reynolds, C. D.; Wood, S. D.; Giordano, F. J. Chem. Soc., Perkin Trans. 1 1993, 451-458.
269. (b) Harrison, D. M.; Sharma, R. B. Tetrahedron 1993, 49, 3165-3184.
270. (a) Bailey, P. D.; McLay, N. R. J. Chem. Soc., Perkin Trans, 1 1993, 441-449.
271. (b) Fu, X.; Cook, J. M. J. Org. Chem. 1993, 58, 661-672.
272. Waldmann, H.; Braun, M,; Weymann, M.; Gewehr, M. Tetrahedron 1993, 49, 397-416.
273. Crich, D.; Lim, L. B. L. Heterocycles 1993, 36, 1199-1204.
274. Zembower, D. E.; Gilbert, J. A.; Ames, M. M. J. Med. Chem. 1993, 36, 305-313.
275. Golebiowski, A.; Jurczak, J. Synlett 1993, 241-245.
276. McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31-33.
277. Roush, W. R.; Brown, B. R. J. Org. Chem. 1993, 58, 2151-2161.
278. van Maarseveen, J. H.; Scheeren, H. W. Tetrahedron 1993, 49, 2325-2344.
279. Knapp, S.; Hale, J. J. J. Org. Chem. 1993, 58, 2650-2651.
280. Hatakeyama, S.; Sugawara, K.; Takano, S. J. Chem. Soc., Chem. Commun. 1993, 125-127.
281. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604-3606.
282. Jurczak, J.; Prokopowicz, P.; Golebiowski, A. Tetrahedron Lett. 1993, 34, 7107-7110.
283. Pauly, R.; Sasaki, N. A.; Potier, P. Tetrahedron Lett. 1994, 35, 237-240.
284. Horikawa, M.; Hashimoto, K.; Shirahama, H. Tetrahedron Lett. 1993, 34, 331-334.
285. Leeson, P. D.; Williams, B. J.; Rowley, M.; Moore, K. W.; Baker, R.; Kemp, J. A.; Priestley, T.; Foster, A. C.; Donald, A. E. Bioorg. Med. Chem. Lett. 1993, 3, 71-76.
286. Griesbeck, A. G.; Mauder, H.; Müller, I.; Peters, E.-M.; Peters, K.; von Schnering, H. G. Tetrahedron Lett. 1993, 34, 453-456.
287. Kelly-Basetti, B. M.; Mackay, M. F.; Pereira, S. M.; Savage, G. P.; Simpson, G. W. Heterocycles 1994, 37, 529-539.
288. Gómez-Monterrey, I.; González-Muñiz, R.; Herranz, R.; García-López, M. T. Tetrahedron Lett. 1993, 34, 3593-3594.
289. Dener, J. M.; Zhang, L.-H.; Rapoport, H. J. Org. Chem. 1993, 58, 1159-1166.
290. Burger, K.; Rudolph, M.; Fehn, S. Angew. Chem., Int. Ed. Engl. 1993, 32, 285-287.
291. Feldman, P. L.; Rapoport, H. J. Org. Chem. 1986, 51, 3882-3890.
292. Whitten, J. P.; Cube, R. V.; Baron, B. M.; McDonald, I. A. Bioorg. Med. Chem. Lett. 1993, 3, 19-22.
293. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 2911-2914.
294. Jefford, C. W.; Wang, J. B. Tetrahedron Lett. 1993, 34, 3119-3122.
295. Wilson, K. J.; Sabat, M.; McGarvey, G. J. J. Org. Chem. 1993, 58, 6180-6181.
296. Nakamura, H.; Oba, Y.; Murai, A. Tetrahedron Lett. 1993, 34, 2779-2782.
297. Fukuyama, T.; Liu, G.; Linton, S. D.; Lin, S.-C.; Nishino, H. Tetrahedron Lett. 1993, 34, 2577-2580.
298. Langlois, N.; Rojas, A. Tetrahedron Lett. 1993, 34, 2477-2480.
299. Langlois, N.; Rojas, A. Tetrahedron 1993, 49, 77-82.
300. Yao, Z.-J.; Wu, Y.-L. Tetrahedron Lett. 1994, 35, 157-160.
301. Ibrahim, H. H.; Lubell, W. D. J. Org. Chem. 1993, 58, 6438-6441.
302. Mulzer, J.; Shanyoor, M. Tetrahedron Lett. 1993, 34, 6545-6548.
303. Matsunaga, N.; Aoyama, T.; Shioiri, T. Heterocycles 1994, 37, 387-400.
304. Wong, P. L.; Moeller, K. D. J. Am. Chem. Soc. 1993, 115, 11434-11445.
305. Jacobi, P. A.; Blum, C. A.; DeSimone, R. W.; Udodong, U. E. S. Tetrahedron Lett. 1989, 30, 7173-7176.