Vinylogous aldol reaction: a valuable, yet understated carbon-carbon bond-forming maneuver

Chemical Reviews

Volumn 100, Issue 6, 2000, Pages 1929-1972

  Casiraghi, Giovanni ^a   Zanardi, Franca ^a   Appendino, Giovanni ^b   Rassu, Gloria ^c  

^a UNIVERSITY OF PARMA   (Italy)

^b UNIVERSITY OF TURIN   (Italy)

^c CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; CATALYST SELECTIVITY; CHEMICAL BONDS; COMPLEXATION; ELECTRONS; ION EXCHANGE; MOLECULAR STRUCTURE; OLEFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CARBON-CARBON BOND; LEWIS ACID; ORGANIC SYNTHESIS; SYNTHETIC ORGANIC CHEMISTRY; VINYLOGOUS ALDOL REACTION;

AROMATIC COMPOUNDS;

EID: 0033690703     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr990247i     Document Type: Article

References (322)

1. For general reviews, see: (a) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, FL, 1984; Vol. 3, pp 111-212.
2. (b) Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 133-179, 181-238.
3. Moon Kim, B.; Williams, S. F.; Masamune, S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 239-275.
4. Paterson, I. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 301-319.
5. (e) Gennari, C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, p 629-660.
6. (f) Braun, M. In Stereoselective Synthesis (Houben-Weyl, Methods of Organic Chemistry); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; GeorgeThieme Verlag: Stuttgart, 1995; Vol. E21b, pp 1603-1666, 1713-1735.
7. (g) Franklin, A. S.; Paterson, I. Contemp. Org. Synth. 1994, 1, 317-338.
8. Compared to its relevance in organic chemistry, there are relatively few reviews on vinylogy. (a) Fuson, R. C. Chem. Rev. 1935, 16, 1-27.
9. (b) Krishnamurthy, S. J. Chem. Educ. 1982, 59, 543-547.
10. Bruneau, P.; Taylor, P. J.; Wilkinson, A. J. J. Chem. Soc., Perkin Trans. 2 1996, 2263-2269.
11. Claisen, L. Ber. 1926, 59, 144-153.
12. Yamamoto, Y. In Stereoselective Synthesis (Houben-Weyl, Methods of Organic Chemistry); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: Stuttgart, 1995; Vol. E21b, pp 2011-2040.
13. Perrier, H.; Bayly, C.; Laliberté, F.; Huang, Z.; Rasori, R.; Robichaud, A.; Girard, Y.; Mcdonald, D. Bioorg. Med. Chem. Lett. 1999, 9, 323-326.
14. Wermuth, C. G. In The Practice of Medicinal Chemistry; Wermuth, C. G., Ed.; Academic Press: London, 1996; pp 181-202.
15. Hagihara, M.; Anthony, N. J.; Stout, T.J.; Clardy, J.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6568-6570.
16. For a general review, see: Little, R. D.; Masjedizadeh, M. R.; Wallquist, O.; McLaughling, J. I. Org. React. 1995, 47, 315-552.
17. (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607-629.
18. (b) Casiraghi, G.; Rassu, G.; Zanardi, F.; Battistini, L. In Advances in Asymmetric Synthesis; Hassner, A., Ed.; JAI Press: Stamford, 1998; Vol. 3, pp 113-189.
19. Rassu, G.; Zanardi, F.; Battistini, L.; Casiraghi, G. Synlett 1999, 1333-1350.
20. An interesting case is that of 2-cyclopentenones, which can easily be deprotonated both at the α′-and y-position, affording resonance-stabilized dianions which are dialkylated by treatment with aldehydes: Koreeda, M.; Liang, Y.; Akagi, H. J. Chem. Soc., Chem. Commun. 1979, 449-450.
21. Seebach, D. Angew. Chem., Int. Ed. Engl. 1979, 18, 239-258.
22. General preparation: (a) Lee, R. A.; McAndrew, C.; Patel, K. M.; Reusch, W. Tetrahedron Lett. 1973, 965-968.
23. (b) Stork, G.; Danheiser, R. J. Org. Chem. 1973, 38, 1775-1776.
24. (a) House, H. O. Modern Synthetic Reactions, 2nd ed.; Benjamin, W. A., Ed.; Menlo Park, CA, 1972; Chapter 9.
25. (b) Carruthers, W. Some Modern Methods of Organic Synthesis; Cambridge University Press: Cambridge, 1986; pp 20-24.
26. D'Angelo, J. Tetrahedron 1976, 32, 2979-2990.
27. Caine, D. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, pp 1-63.
28. Stork, G.; Kraus, G. A. J. Am. Chem. Soc. 1976, 97, 2351-2352.
29. Stork, G.; Benaim, J. J. Am. Chem. Soc. 1971, 93, 5938-5939.
30. Velluz, L.; Nominé, G.; Mathieu, J. Angew. Chem. 1960, 72, 725-730.
31. Cordell, G. A. Introduction to Alkaloids; Wiley: New York, 1981; pp 826-828.
32. Pakrashi, S. C.; Mukhopadhyay, R.; Chosh Dastidar, P. P.; Bhattacharjya, A.; Ali, E. Tetrahedron Lett. 1983, 24, 291-294.
33. Cordell, G. A. In Introduction to Alkaloids; Wiley: New York, 1981; p 555.
34. (a) Jeffs, P. W.; Campbell, H. F.; Farrier, D. S.; Ganguli, G.; Martin, N. H.; Molina, G. Phytochemistry 1974, 13, 933-945.
35. For a review on the Sceletium alkaloids, see: (b) Popelak, A.; Lettenbauer, G. In The Alkaloids; Manske, R. H. F., Ed.; Academic Press: New York, 1967; Vol. 9, pp 467-481.
36. Barret, A. G.; Barton, D. H. R.; Franckowiak, G.; Papaioannou, D.; Widdowson, D. A. J. Chem. Soc. Perkin Trans. 1 1979, 662-668. See also: Cordell, G. A. In Introduction to Alkaloids; Wiley: New York, 1981; pp 462-463.
37. Barret, A. G.; Barton, D. H. R.; Franckowiak, G.; Papaioannou, D.; Widdowson, D. A. J. Chem. Soc. Perkin Trans. 1 1979, 662-668. See also: Cordell, G. A. In Introduction to Alkaloids; Wiley: New York, 1981; pp 462-463.
38. Maier, U. H.; Rödl, W.; Deus-Neumann, B.; Zenk, M. H. Phytochemistry 1999, 52, 373-382.
39. Pary, R. J.; Chang, M. N. T.; Schwab, J. M.; Foxman, B. M. J. Am. Chem. Soc. 1980, 102, 1099-1111.
40. For a review, see: Mia, M. A. J.; Hudlicky, T.; Reed, J. W. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1998; Vol. 51, pp 199-269.
41. Battersby, A. R.; Sheldrake, P. W.; Milner, J. A. Tetrahedron Lett. 1974, 3315-3318.
42. Appendino, G.; Jakupovic, S.; Tron, G. C.; Jakupovic, J.; Millon, V.; Ballero, M. J. Nat. Prod. 1998, 61, 749-756.
43. For a review, see: Gröger, D.; Floss, H. G. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 172-218.
44. Takahashi, T. Yakugaku Zasshi 1931, 51, 401-405.
45. For a review, see: Appendino, G. In The Chemistry and Pharmacology of Taxol and its Derivatives; Farina, V., Ed.; Elsevier: Amsterdam, 1995; pp 7-53.
46. Appendino, G.; Fenoglio, I.; Vander Velde, D. G. J. Nat. Prod. 1997, 60, 464-466.
47. Zamir, L. O.; Cherestes, A. D.; Nikolakakis, A.; Sauriol, F.; Mamer, O. Tetrahedron Lett. 1999, 40, 7917-7920.
48. Pinciroli, V.; Ceccarelli, W.; Fuser-Bassini, D.; Menichincheri, M.; Mongelli, N.; Vanotti, E. Tetrahedron Lett. 1996, 37, 9365-9368.
49. Jacobi, P.; Härle, E.; Schairer, H. U.; Hecker, E. Liebigs Ann. Chem. 1970, 741, 13-32.
50. Hecker, H.; Schimdt, R. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebaeh, H., Kirby, G. W., Eds.; 1974; Vol 31, pp 377-467.
51. Cole, R. J.; Kirksey, J. W.; Clardy, J.; Eickman, N.; Weinreb, S. M.; Singh, P.; Kim, D. Tetrahedron Lett. 1976, 43, 3849-3852.
52. Baldwin, J. E.; Beyeler, A.; Cox, R. J.; Keats, C.; Pritchard, G. J.; Adlington, R. M.; Watkin, D. J. Tetrahedron 1999, 55, 7363-7374
53. McMorris, T. C.; Keiner, M. J.; Wang, W.; Yu, J.; Estes, L. A.; Taetle, R. J. Nat. Prod. 1996, 59, 896-899.
54. McMorris, T. C. Bioorg. Med. Chem. 1999, 7, 881-886.
55. Anchel, M.; Hervey, A.; Robbins, W. J. Proc. Natl. Acad. Sci. U.S.A. 1950, 36, 300-305.
56. (a) McLeod, F. Am. Chem. J. 1907, 37, 20-23.
57. (b) Smedley, I. J. Chem. Soc. 1911, 99, 1627-1633.
58. (a) Fischer, F. G.; Hultzsch, K.; Falig, W. Ber. 1937, 70, 370-375.
59. (b) Kuhn, R.; Grundmann, G. Ber. 1938, 71, 2274-2277.
60. Du Mont, H. L.; Fleischauer, H. Ber. 1938, 71, 1958-1962.
61. Meerwein, H.; von Bock, B.; Kirschnick, B.; Lenz W.; Migge, A. J. Prakt. Chem. 1936, 147, 211-225.
62. (a) Delépine, M. Ann. Chim. (Paris) 1910, 20, 389-398.
63. (b) Jacques, J. Ann. Chim. (Paris) 1945, 20, 322-366.
64. Blanc, P. Y. Helv. Chim. Acta 1958, 41, 625-634.
65. Pummerer, R.; Aldebert, F.; Büttner, F.; Graser, F.; Pirson, E.; Rick, H.; Sperber, H. Ann. 1953, 583, 161-183.
66. Devitt, P. F.; Philbin, E. M.; Wheeler, T. S. J. Chem. Soc. 1958, 510-512.
67. Miller, R. E.; Nord, F. F. J. Org. Chem. 1951, 16, 1380-1388.
68. (a) Wallach, O. Ber. 1896, 29, 1595-1601.
69. (b) Wallach, O. Ann. 1899, 305, 261-276.
70. Wallach, O. Ann. 1913, 397, 211-216.
71. Müller, A. Ber. 1921, 54, 1471-1481.
72. (e) Christ, R. E.; Fuson, R. C. J. Am. Chem. Soc. 1937, 59, 893-897.
73. (a) Dewar, J.; Morrison, D. R.; Read, J. J. Chem. Soc. 1936, 1598-1600.
74. (b) Conia, J. M.; O'Leary, U. Compt. Rend. Acad. Sci. Fr. 1959, 249, 1002-1004.
75. Kabass, G. Tetrahedron 1966, 22, 1213-1218.
76. Sugiyama, N.; Yamamoto, M.; Kashima, C. Bull. Chem. Soc. Jpn. 1970, 43, 3937-3938.
77. Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 152-153.
78. Mayer, R. Ber. 1956, 89, 1443-1454.
79. Kunze, K. Ber. 1926, 59, 2085-2088.
80. Paquette, L. A. Eur. J. Org. Chem. 1998, 1709-1728.
81. Gaidamovich, N. N.; Torgov, I. V. Izv. Acad. Nauk SSSR 1964, 1311 (C.A. 1964, 61, 8203).
82. Gaidamovich, N. N.; Torgov, I. V. Izv. Acad. Nauk SSSR 1964, 1311 (C.A. 1964, 61, 8203).
83. Schulze, A.; Oediger, H. Liebigs Ann. Chem. 1981, 1725-1727.
84. Stowell, J. C. Carbanions in Organic Synthesis; Wiley: New York, 1979; pp 10-18 and references therein.
85. An important exception is the enolate of acetaldehyde, which can be easily prepared from tetrahydrofuran, see: Jung, M. E.; Blum, R. B. Tetrahedron Lett. 1977, 3791-3794.
86. Saito, S.; Shiozawa, M.; Ito, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813-814.
87. (a) de Graaf, S. A. G.; Oosterhoff, P. E. R.; van der Gen, A. Tetrahedron Lett. 1974, 153-1656.
88. (b) Groenewegen, P.; Kallenberg, H.; van der Gen, A. Tetrahedron Lett. 1978, 491-494.
89. The dienolate of crotonaldehyde could be stored for two years in liquid ammonia without degradation (!). Quoted in ref 59a.
90. Vedejs, E.; Gapinski, D. M. Tetrahedron Lett. 1981, 22, 4913-1916.
91. 2-DMF-THF (Kawanisi, M.; Itoh, Y.; Hieda, T.; Kozima, S.; Hitomi, T.; Kobayashi, K. Chemistry Lett. 1985, 647-650).
92. 2-DMF-THF (Kawanisi, M.; Itoh, Y.; Hieda, T.; Kozima, S.; Hitomi, T.; Kobayashi, K. Chemistry Lett. 1985, 647-650).
93. 2-DMF-THF (Kawanisi, M.; Itoh, Y.; Hieda, T.; Kozima, S.; Hitomi, T.; Kobayashi, K. Chemistry Lett. 1985, 647-650).
94. 2-DMF-THF (Kawanisi, M.; Itoh, Y.; Hieda, T.; Kozima, S.; Hitomi, T.; Kobayashi, K. Chemistry Lett. 1985, 647-650).
95. 2-DMF-THF (Kawanisi, M.; Itoh, Y.; Hieda, T.; Kozima, S.; Hitomi, T.; Kobayashi, K. Chemistry Lett. 1985, 647-650).
96. 2-DMF-THF (Kawanisi, M.; Itoh, Y.; Hieda, T.; Kozima, S.; Hitomi, T.; Kobayashi, K. Chemistry Lett. 1985, 647-650).
97. 2-DMF-THF (Kawanisi, M.; Itoh, Y.; Hieda, T.; Kozima, S.; Hitomi, T.; Kobayashi, K. Chemistry Lett. 1985, 647-650).
98. 2-DMF-THF (Kawanisi, M.; Itoh, Y.; Hieda, T.; Kozima, S.; Hitomi, T.; Kobayashi, K. Chemistry Lett. 1985, 647-650).
99. Stork, G.; Hudrlik, P. F. J. Am. Chem. Soc. 1968, 90, 4464-4465.
100. House, H. O.; Czuba, L. J.; Gall, M.; Olmstead, H. D. J. Org. Chem. 1969, 34, 2324-2336.
101. Duhamel, P.; Cahard, D.; Poirier, J.-M. J. Chem. Soc., Perkin Trans. 1 1993, 2509-2511.
102. Cahard, D.; Duhamel, L.; Lecomte, S.; Poirier, J.-M. Synlett 1998, 1399-1401.
103. Cahard, D.; Poirier, J.-M.; Duhamel, P. Tetrahedron Lett. 1998, 39, 7093-7096.
104. Si-Fodil, M.; Ferreira, H.; Galak, J.; Duhamel, L. Tetrahedron Lett. 1998, 39, 8975-8978.
105. Paterson, I.; Smith, J. D. J. Org. Chem. 1992, 57, 3261-3264.
106. Hatanaka, Y., Kuwajima, I. J. Org. Chem. 1986, 57, 1932-1934.
107. For leading references, see: (a) Colvin E. W. Silicon in Organic Synthesis; Butterworth: London, 1981; pp 97-124.
108. (b) Chan, T. H.; Fleming, I. Synthesis 1979, 761-786.
109. Sakurai, H. Pure Appl. Chem. 1982, 54, 1-22.
110. (a) Bellassoued, M.; Salemkour, M. Tetrahedron 1996, 52, 4607-4624.
111. (b) Bellassoued, M.; Reboul, E.; Salemkour, M. Synth. Commun. 1995, 25, 3097-3108.
112. Horiguchi, Y.; Furukawa, T.; Kuwajima, I. J. Am. Chem. Soc. 1989, 111, 8277-8279.
113. Ooi, T.; Kondo, Y.; Maruoka, K. Angew. Chem., Int. Ed. Engl. 1998, 37, 3039-3041.
114. Quoted in Majewski, M.; Mpango, G. B.; Thomas, M. T.; Wu, A.; Snieckus, V. J. Org. Chem. 1981, 46, 2029-2045. The important base LDA was introduced by Creger (Parke Davis and Co.) in a publication describing the alkylation of the dianion of isobutyric acid (Creger, P. L. J. Am. Chem. Soc. 1967, 89, 2500-2501).
115. Quoted in Majewski, M.; Mpango, G. B.; Thomas, M. T.; Wu, A.; Snieckus, V. J. Org. Chem. 1981, 46, 2029-2045. The important base LDA was introduced by Creger (Parke Davis and Co.) in a publication describing the alkylation of the dianion of isobutyric acid (Creger, P. L. J. Am. Chem. Soc. 1967, 89, 2500-2501).
116. Ivanov, D.; Vassiliev, G.; Panayotov, I. Synthesis 1975, 83-98.
117. Henrich, C. A.; Dilly, W. W.; McKean, D. R.; Baggiolini, E.; Siddal, J. B. J. Org. Chem. 1975, 40, 8-14.
118. Cardillo, G.; Orena, M.; Sandri, S. Tetrahedron 1976, 32, 107-108.
119. Cainelli, G.; Cardillo, G.; Contento, M.; Grasselli, P.; Umani Ronchi, A. Gazz. Chim. Ital. 1973, 103, 117-125.
120. (a) Creger, P. J. Am. Chem. Soc. 1967, 89, 2500-2501.
121. (b) Creger, P. J. Am. Chem. Soc. 1970, 92, 1396-1398.
122. Cainelli, G.; Cardillo, G.; Contento, M.; Trapani, G.; Umani Ronchi, A. J. Chem. Soc. Perkin Trans. 1 1973, 400-404.
123. Casinos, I.; Mestres, R. J. Chem. Soc., Perkin Trans. 1 1978, 1651-1655.
124. Bank, S. J. Am. Chem. Soc. 1965, 87, 3245-3246.
125. 1,3 strain (Boerth, D. W.; Streitwiser, A., Jr. J. Am. Chem. Soc. 1978, 100, 750-754) or because of its proposed "aromaticity" (Schleyer, P. v. R.; Dill, J. D.; Pople, J. A.; Hehre, W. J. Tetrahedron 1977, 33, 2497-2501).
126. 1,3 strain (Boerth, D. W.; Streitwiser, A., Jr. J. Am. Chem. Soc. 1978, 100, 750-754) or because of its proposed "aromaticity" (Schleyer, P. v. R.; Dill, J. D.; Pople, J. A.; Hehre, W. J. Tetrahedron 1977, 33, 2497-2501).
127. Vedejs, E.; Gapinski, D. M.; McElvain, S. M. Tetrahedron Lett. 1981, 4913-4916.
128. In these conditions, ethyl crotonate was also to be found only partly ionized: Rathke, M. W.; Sullivan, D. Tetrahedron Lett. 1972, 4249-4252.
129. Itoh, K.; Fukui, M.; Kurachi, Y. J. Chem. Soc., Chem. Commun. 1977, 500-501.
130. Frater, G. In Stereoselective Synthesis (Houben-Weyl, Methods of Organic Chemistry); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; George Thieme Verlag: Stuttgart, 1995; Vol. E21a, pp 723-726 and references therein.
131. For early studies, see: (a) Wilson, S. R.; Myers, R. S. J. Org. Chem. 1975, 40, 3309-3311.
132. (b) Fréter, G. Helv. Chim. Acta 1975, 58, 442-447.
133. Fréter, G. Helv. Chim. Acta 1978, 61, 2709-2719.
134. Successful deprotonation of γ-monosubstituted α,α-unsaturated esters has sometimes been achieved, see also: Haynes, R. K.; Lam, R. W.-L.; Yeung, L.-L.; Williams, I. D.; Ridley, A. C.; Starling, S. M.; Vonwiller, S. C.; Hambley, T. W.; Lelandais, P. J. Org. Chem. 1997, 62, 4552-4553.
135. Herrmann, J. L.; Kieczykowski, G. R.; Schlessinger, R. H. Tetrahedron Lett. 1973, 2433-2436.
136. Haag, D.; Chen, X.-T.; Fraser-Reid, B. Chem. Commun. 1998, 2577-2578.
137. Harris, F. L.; Weiler, L. Tetrahedron Lett. 1984, 25, 1333-1335.
138. Dugger, R. W.; Heathcock, C. H. J. Org. Chem. 1980, 45, 1181-1185.
139. Kajikawa, A.; Morisaki, M.; Ikekawa, N. Tetrahedron Lett. 1975, 4135-4136.
140. Anghelova, Y. Synthesis 1974, 343-344.
141. Majewski, M.; Mpango, G. B.; Thomas, M. T.; Wu, A.; Snieckus, V. J. Org. Chem. 1981, 46, 2029-2045.
142. Schofield, K. Hetero-Aromatic Nitrogen Compounds; Butterworths: London, 1967; p 311.
143. Atal, C. K.; Dhar, K. L.; Singh, J. Lloydia 1975, 38, 256-264.
144. Dwuma-Badu, D.; Ayim, J. S. K.; Dabra, T. T.; El-Sohly, H. N.; Knapp, J. E.; Slatkin, D. J.; Sniff, P. L., Jr. Lloydia 1976, 39, 60-64.
145. (a) Tomooka, K.; Nagasawa, A.; Wei, S.-Y.; Nakai, T. Tetrahedron Lett. 1996, 37, 8899-8900.
146. (b) Sugiura, M.; Yagi, Y.; Wei, S.-Y.; Nakai, T. Tetrahedron Lett. 1998, 39, 4351-4354.
147. Black, W. C.; Giroux, A.; Greidames, G. Tetrahedron Lett. 1996, 37, 4471-4474.
148. Mukaiyama, T.; Kobayashi, S. Org. React. 1994, 46, 1-103.
149. Yoshimoto, M.; Ishida, N.; Hiraoka, T. Tetrahedron Lett. 1973, 39-42.
150. For a review, see: Pattenden, G. In Forsch. Chem. org. Naturstoffe; Herz, W., Grisebach, H., Kirby, G. W., Eds.; 1978; Vol 35, pp 133-198.
151. (a) Bryson, T. A.; Gamill, R. B. Tetrahedron Lett. 1974, 3963-3966.
152. (b) Telschow, J. E.; Reusch, W. J. Org. Chem. 1975, 40, 862-865.
153. (a) Angelova, Y.; Ivanov, C.; Metsov, S. Chem. Ber. 1977, 10, 1594-1596.
154. (b) Smissman, E. E.; Voldeng, A. N. J. Org. Chem. 1964, 29, 3161-3165.
155. Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 2317-2320.
156. Brown, D. W.; Campbell, M. M.; Taylor, A. P.; Zhang, X.-a. Tetrahedron Lett. 1987, 28, 985-988.
157. For a review on the biological properties of geiparvarin and analogues, see: Valenti, P. Fitoterapia 1997, 68, 115-126.
158. Smith, A. B., III; Jerris, P. J. Tetrahedron Lett. 1980, 21, 711-714.
159. Ojima, N.; Takenaka, S.; Seto, S. Phytochemistry 1973, 12, 2527-2529.
160. Claisen, L.; Ewan, T. Annalen 1895, 284, 245-299.
161. Knight, D. W.; Pattenden, G. J. Chem. Soc., Perkin Trans. I 1979, 70-76.
162. Fell, S. C. M.; Heaps, J.; Holker, J. S. E. J. Chem. Soc., Chem. Commun. 1979, 81-82.
163. Hänsel, R.; Pelter, A. Phytochemistry 1971, 10, 1627-1634.
164. Pelter, A.; Al-Bayati, R. I. H.; Hänsel, R.; Dinter, H.; Burke, B. Tetrahedron Lett. 1981, 22, 1545-1548.
165. Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hänsel, R. J. Chem. Soc. Perkin Trans. 1 1987, 717-742.
166. For Grignard reactions in wet ether, see: Smith, D. H. J. Chem. Ed. 1999, 76, 1427-1428.
167. Kende, A. S.; Smalley, T. L., Jr.; Huang, H. J. Am. Chem. Soc. 1999, 121, 7431-7432.
168. Kono, Y.; Gardner, J. M.; Kobayashi, K.; Suzuki, Y.; Takeuchi, S.; Sakurai, T. Phytochemistry 1986, 25, 69-72.
169. Mulzer, J.; Dupré, S.; Buschmann, J.; Luger, P. Angew. Chem., Int. Ed. Engl. 1993, 32, 1452-1454.
170. Paterson, J.; Wallace, D. J.; Cowden, C. J. Synthesis 1998, 639-652.
171. (a) Crimmins, M. T.; Washburn, D. G.; Katz, J. D.; Zawacki, F. J. Tetrahedron Lett. 1998, 39, 3439-3442.
172. (b) Crimmins, M. T.; Washburn, D. G. Tetrahedron Lett. 1998, 39, 7487-7490.
173. Crimmins, M. T.; O'Mahony, R. J. Org. Chem. 1990, 55, 5894-5900.
174. Pettit, G. R.; Cichacz, Z. A.; Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.; Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302-1304.
175. This seminal discovery was first disclosed in 1986, see: Schlessinger, R. H.; Iwanowicz E. J.; Springer, J. P. J. Org. Chem. 1986, 51, 3070-3073.
176. Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1999, 40, 1257-1260.
177. Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1996, 31, 1331-1334.
178. Schlessinger, R. H.; Li, Y.-J. J. Am. Chem. Soc. 1996, 118, 3301-3302. For a previous synthetic work by this group on the synthesis of this compound, see ref 24.
179. Schlessinger, R. H.; Pettus, L. H. J. Org. Chem. 1998, 63, 9089-9094.
180. (a) Dankwardt, S. M.; Dankwardt, J. W.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4971-4974.
181. (b) Dankwardt, S. M.; Dankwardt, J. W.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4975-4978.
182. Dankwardt, S. M.; Dankwardt, J. W.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4979-4982.
183. Dankwardt, S. M.; Dankwardt, J. W.; Schlessinger, R. H. Tetrahedron Lett. 1998, 39, 4983-4986.
184. Schlessinger, R. H.; Li, Y.-J.; Von Langen, D. J. J. Org. Chem. 1996, 61, 3226-3227.
185. Nolde, C.; Lawesson, S. O. Bull. Soc. Chim. Belg. 1977, 86, 313-319.
186. (a) Whitesell, J. K.; Felman, S. W. J. Org. Chem. 1977, 42, 1663-1664.
187. (b) Harding, K. E.; Burks, S. R. J. Org. Chem. 1981, 46, 3920-3922.
188. Enders, D.; Kipphardt, H.; Gerdes, P.; Brenak-Valle, L. J.; Bhushan, V. Bull. Soc. Chim. Belg. 1988, 97, 691-704.
189. Schlessinger, R. H.; Mjalli, A. M. M.; Adams, A. D.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1992, 57, 2992-2993.
190. (a) Mukaiyama, T.; Narasaka, K.; Banno, K. Chem. Lett. 1973, 1011-1014.
191. (b) Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am. Chem. Soc. 1974, 96, 7503-7509.
192. See also: (c) Costa, A. L.; Tagliavini, E. In Seminars in Organic Synthesis; Societá Chimica Italiana: Milano, 1996; pp 185-210.
193. For recent examples of synthetic applications of the Mukaiyama aldol reaction, see: (a) Evans, D. A.; Burgey, C. S.; Paras, N. A.; Vojkovsky, T.; Tregay, S. W. J. Am. Chem. Soc. 1998, 120, 5824-5825.
194. (b) Denmark, S. E.; Wong, K.-T.; Stavenger, R. A. J. Am. Chem. Soc. 1997, 119, 2333-2334.
195. Kobayashi, S.; Uchiro, H.; Shiina, I.; Mukaiyama, T. Tetrahedron 1993, 49, 1761-1772.
196. Corey, E. J.; Cywin, C. L.; Roper, T. D. Tetrahedron Lett. 1992, 33, 6907-6910.
197. (a) Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 319-322.
198. (b) Ishida, A.; Mukaiyama, T. Chem. Lett. 1975, 1167-1170.
199. Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 1161-1168.
200. (a) Ishida, A.; Mukaiyama, T. Chem. Lett. 1977, 467-470.
201. (b) Ishida, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1978, 51, 2077-2081.
202. Mukaiyama, T.; Ishida, A. Chem. Lett. 1975, 1201-1202.
203. Bellassoued, M.; Ennigrou, R.; Gaudemar, M. J. Organomet. Chem. 1988, 338, 149-158.
204. (a) Chan, T.-H.; Brownbridge, P. J. Chem. Soc. Chem. Commun. 1979, 578-579.
205. (b) Brownbridge, P.; Chan, T.-H.; Brook, M. A.; Kang, G. J. Can. J. Chem. 1983, 61, 688-693.
206. Brownbridge, P.; Chan, T.-H. Tetrahedron Lett. 1979, 20, 4437-4440.
207. Lee, S. D.; Chan, T.-H. Tetrahedron 1984, 40, 3611-3616.
208. See also: (e) Yamamoto, K.; Suzuki, S.; Tsuji, J. Chem. Lett. 1978, 649-652.
209. Chan, T.-H.; Brownbridge, P. J. Chem. Soc., Chem. Commun. 1981, 20-21.
210. (a) Fleming, I.; Goldhill, J.; Paterson, I. Tetrahedron Lett. 1979, 20, 3209-3212.
211. (b) Fleming, I.; Lee, T. V. Tetrahedron Lett. 1981, 22, 705-708.
212. For a seminal work dealing with regioselective generation of silyl dienol ethers from enones, see; Krafft, M. E.; Holton, R. A. J. Am. Chem. Soc. 1984, 106, 7619-7621.
213. Takazawa, O.; Tamura, H.; Kogami, K.; Hayashi, K. Bull. Chem. Soc. Jpn. 1982, 55, 1907-1911.
214. Yoshii, E.; Koizumi, T.; Kitatsuji, E.; Kawazoe, T.; Kaneko, T. Heterocycles 1976, 4, 1663-1668.
215. (a) Asaoka, M.; Sugimura, N.; Takei, H. Bull. Chem. Soc. Jpn. 1979, 52, 1953-1956.
216. (b) Asaoka, M.; Yanagida, N.; Takei, H. Tetrahedron Lett. 1980, 21, 4611-4614.
217. Asaoka, M.; Yanagida, N.; Ishibashi, K.; Takei, H. Tetrahedron Lett. 1981, 22, 4269-4270.
218. Negishi, E.-I.; Kotora, M. Tetrahedron 1997, 53, 6707-6738.
219. (a) Fiorenza, M.; Ricci, A.; Romanelli, M. N.; Taddei, M.; Dembech, P.; Seconi, G. Heterocycles 1982, 19, 2327-2329.
220. (b) Fiorenza, M.; Reginato, G.; Ricci, A.; Taddei, M. J. Org. Chem. 1984, 49, 551-553.
221. (a) Jefford, C. W.; Jaggi, D.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4037-4040.
222. (b) Jefford, C. W.; Jaggi, D.; Bernardinelli, G.; Boukouvalas, J. Tetrahedron Lett. 1987, 28, 4041-4044.
223. Boukouvalas, J., Maltais, F. Tetrahedron Lett. 1995, 36, 7175-7176.
224. Boukouvalas, J.; Maltais, F. Tetrahedron Lett. 1994, 35, 5769-5770.
225. Boukouvalas, J.; Maltais, F.; Lachance, N. Tetrahedron Lett. 1994, 35, 7897-7900.
226. Boukouvalas, J.; Lachance, N.; Quellet, M.; Trudeau, M. Tetrahedron Lett. 1998, 39, 7665-7668.
227. Xu, D.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 4685-4688.
228. Von der Ohe, F.; Bruckner, R. Tetrahedron Lett. 1998, 39, 1909-1910.
229. For a complete overview on this subject matter, see ref 9b.
230. A recent review dealing with the Mannich reaction and its modern variants, including a small section on vinylogous applications, has recently appeared: Arend, M.; Westermann, B.; Risch, N. Angew. Chem., Int. Ed. 1998, 37, 1044-1070.
231. Brandstadter, S. M.; Ojima, I.; Hirai, K. Tetrahedron Lett. 1987, 28, 613-616.
232. (a) Mladenova, M.; Bellassoued, M. Synth. Commun. 1993, 23, 725-736.
233. (b) Bellassoued, M.; Ennigrou, R.; Gil, R.; Lensen, N. Synth. Commun. 1998, 28, 3955-3964.
234. Stevens, R. V.; Pruitt, J. R. J. Chem. Soc., Chem. Commun. 1983, 1425.
235. (a) Martin, S. F.; Corbett, J. W. Synthesis 1992, 55-57.
236. (b) Martin, S. F.; Bur, S. K. Tetrahedron Lett. 1997, 38, 7641-7644.
237. For a similar approach to pyrrolidinyl lactone systems, see: Morimoto, Y.; Nishida, K.; Hayashi, Y.; Shirahama, H. Tetrahedron Lett. 1993, 34, 5773-5776.
238. Martin, S. F.; Clark, C. W.; Ito, M.; Mortimore, M. J. Am. Chem. Soc. 1996, 118, 9804-9805.
239. Martin, S. F.; Liras, S. J. Am. Chem. Soc. 1993, 115, 10450-10451.
240. (a) Degiorgis, F.; Lombardo, M.; Trombini, C. Synthesis 1997, 1243-1245.
241. (b) Camiletti, C.; Poletti, L.; Trombini, C. J. Org. Chem. 1994, 59, 6843-6846.
242. Camiletti, C.; Dhavale, D. D.; Donati, F.; Trombini, C. Tetrahedron Lett. 1995, 36, 7293-7296.
243. Mahrwald, R. Chem. Rev. 1999, 99, 1095-1120.
244. Rassu, G.; Auzzas, L.; Pinna, L.; Zanardi, F.; Battistini, L.; Casiraghi, G. Org. Lett. 1999, 1, 1213-1215.
245. Rassu, G.; Spanu, P.; Pinna, L.; Zanardi, F.; Casiraghi, G. Tetrahedron Lett. 1995, 36, 1941-1944.
246. (a) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. J. Org. Chem. 1991, 56, 6523-6527.
247. (b) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P. J. Chem. Soc. Chem. Commun. 1991, 603-604.
248. Casiraghi, G.; Ulgheri F.; Spanu, P.; Rassu, G.; Pinna, L.; Gasparri Fava, G.; Belicchi Ferrari, M.; Pelosi, G. J Chem. Soc., Perkin Trans. 1 1993, 2991-2997.
249. Sato, M.; Sugita, Y.; Abiko, Y.; Kaneko, C. Tetrahedron: Asymmetry 1992, 3, 1157-1160.
250. Evans, D. A.; Ripin, D. H. B.; Halstead, D. P.; Campos, K. R. J. Am. Chem. Soc. 1999, 121, 6816-6826.
251. Evans, D. A.; Carter, P. H.; Carreira, E. M.; Charette, A. B.; Prunet, J. A.; Lautens, M. J. Am. Chem. Soc. 1999, 121, 7540-7552.
252. Evans, D. A.; Black, C. J. Am. Chem. Soc. 1993, 115, 4497-4513.
253. (a) Enders, D.; Burkamp, F.; Runsink, J. Chem. Commun. 1996, 609-610.
254. See also: (b) Reetz, M. T. Chem. Rev. 1999, 99, 1121-1162.
255. Hashiguchi, S.; Kawada, A.; Natsugari, H. J. Chem. Soc., Perkin Trans. 1 1991, 2435-2444.
256. Hagiwara, H.; Kimura, K.; Uda, H. J. Chem. Soc., Perkin Trans. 1 1992, 693-700.
257. (a) Martin, S. F.; Clark, C. W.; Corbett, J. W. J. Org. Chem. 1995, 60, 3236-3242.
258. (b) Martin, S. F.; Chen, K. X.; Eary, C. T. Org. Lett. 1999, 1, 79-81.
259. (a) Martin, S. F.; Barr, K. J. J. Am. Chem. Soc. 1996, 118, 3299-3300.
260. (b) Martin, S. F.; Barr, K. J.; Smith, D. W.; Bur, S. K. J. Am. Chem. Soc. 1999, 121, 6990-6997.
261. Hanessian, S.; McNaughton-Smith, G. Bioorg. Med. Chem. Lett. 1996, 6, 1567-1572.
262. Hanessian, S.; Reddy, G. B. Bioorg. Med. Chem. Lett. 1994, 4, 2285-2290.
263. Hanessian, S.; Raghavan, S. Bioorg. Med. Chem. Lett. 1994, 4, 1697-1702.
264. Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L.; Ulgheri, F. J. Org. Chem. 1993, 58, 3397-3400.
265. Battistini, L.; Rassu, G.; Pinna, L.; Zanardi, F.; Casiraghi, G. Tetrahedron: Asymmetry 1999, 10, 765-773.
266. (a) Molander, G. A.; Cameron, K. O. J. Am. Chem. Soc. 1993, 115, 830-846.
267. (b) Molander, G. A.; Siedem, C. S. J. Org. Chem. 1995, 60, 130-138.
268. Molander, G. A.; Cameron, K. O. J. Org. Chem. 1993, 58, 5931-5943.
269. (a) Molander, G. A.; Eastwood, P. R. J. Org. Chem. 1995, 60, 4559-4565.
270. (b) Molander, G. A.; Bessières, B.; Eastwood, P. R.; Noll, B. C. J. Org. Chem. 1999, 64, 4124-4129.
271. Molander, G. A.; Haas, J. Tetrahedron 1999, 55, 617-624.
272. Ko, S. Y.; Lerpiniere, J. Tetrahedron Lett. 1995, 36, 2101-2104.
273. Solladié, G.; Hanquet, G.; Rolland, C. Tetrahedron Lett. 1999, 40, 177-180.
274. Lemée, L.; Jégou, A.; Veyrières, A. Tetrahedron Lett. 1999, 40, 2761-2764.
275. A related C-glycosylation protocol has been developed to join a butenolide moiety to glucopyranose oxocarbenium ions: Jégou, A.; Veyrières, A. Tetrahedron: Asymmetry 1998, 9, 3129-3134.
276. (a) Alali, F. Q.; Liu, X.-X.; McLaughlin, J. L. J. Nat. Prod. 1999, 62, 504-540.
277. (b) Cave, A.; Figadère, B.; Laurens, A.; Cortes, D. In Progress in the Chemistry of Organic Natural Products; Hertz, W., Ed.; Springer-Verlag: Wien, New York, 1997; Vol. 70, pp 81-288.
278. Casiraghi, G.; Zanardi, F.; Battistini, L.; Rassu, G.; Appendino, G. ChemTracts-Org. Chem. 1998, 11, 803-827 and references therein.
279. (a) Figadère, B.; Peyrat, J.-F.; Cavé, A. J. Org. Chem. 1997, 62, 3428-3429.
280. (b) Figadère, B.; Chaboche, C.; Peyrat, J.-F.; Cavé, A. Tetrahedron Lett. 1993, 34, 8093-8096.
281. Koert, U.; Stein, M.; Harms, K. Tetrahedron Lett. 1993, 34, 2299-2302.
282. (a) Zanardi, F.; Battistini, L.; Rassu, G.; Pinna, L.; Mor, M.; Culeddu, N.; Casiraghi, G. J. Org. Chem. 1998, 63, 1368-1369.
283. (b) Zanardi, F.; Battistini, L.; Rassu, G.; Auzzas, L.; Pinna, L.; Marzocchi, L.; Acquotti, D.; Casiraghi, G. J. Org. Chem. 2000, 65, 2048-2064.
284. Pichon, M.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1996, 37, 7963-7966.
285. Pichon, M.; Hocquemiller, R.; Figadère, B. Tetrahedron Lett. 1999, 40, 8567-8570.
286. Hanessian, S.; Abad Grillo, T. J. Org. Chem. 1998, 63, 1049-1057.
287. (a) Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc. 1994, 116, 2139-2140.
288. See also: (b) Uno, H.; Baldwin, J. E.; Churcher, I.; Russell, A. T. Synlett 1997, 390-392.
289. (a) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113-116.
290. (b) Omura, S.; Matsuzaki, K.; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117-118.
291. Baussanne, I.; Royer, J. Tetrahedron Lett. 1996, 37, 1213-1216.
292. Baussanne, I.; Schwardt, O.; Royer, J.; Pichon, M.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1997, 38, 2259-2262.
293. Dudot, B.; Micouin, L.; Baussanne, I.; Royer, J. Synthesis 1999, 688-694.
294. (a) Poli, G.; Ciofi, S.; Maccagni, E.; Sardone, N. Tetrahedron Lett. 1995, 36, 8669-8672.
295. (b) Poli, G.; Ciofi Baffoni, S.; Gianbastiani, G.; Reginato, G. Tetrahedron 1998, 54, 10403-10418.
296. Ceccarelli, S.; Piarummi U.; Gennari, C. Tetrahedron Lett. 1999, 40, 153-156.
297. Danishefsky, S.; Prisbylla, M.; Lipisko, B. Tetrahedron Lett. 1980, 21, 805-808.
298. Caputo, R.; Ferreri, C.; Mastroianni, D.; Palumbo, G.; Wenkert, E. Synth. Commun. 1992, 22, 2305-2312.
299. Kataoka, Y.; Nakamura, Y.; Morihira, K.; Arai, H.; Horiguchi, Y.; Kuwajima, I. Tetrahedron Lett. 1992, 33, 6979-6982.
300. Furukawa, T.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. Tetrahedron 1992, 48, 6975-6984.
301. Seto, M.; Morihira, K.; Katagiri, S.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. Chem. Lett. 1993, 133-136.
302. Seto, M.; Morihira, K.; Horiguchi, Y.; Kuwajima, I. J. Org. Chem. 1994, 59, 3165-3174.
303. Nakamura, T.; Waizumi, N.; Tsuruta, K.; Horiguchi, Y.; Kuwajima, I. Synlett 1994, 584-586.
304. Morihira, K.; Hara, R.; Kawahara, S.; Nishimori, T.; Nakamura, N.; Kusama, H.; Kuwajima, I. J. Am. Chem. Soc. 1998, 120, 12980-12981.
305. Hara, R.; Furukawa, T.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1996, 118, 9186-9187.
306. Hara, R.; Furukawa, T.; Kashima, H.; Kusama, H.; Horiguchi, Y.; Kuwajima, I. J. Am. Chem. Soc. 1999, 121, 3072-3082.
307. For a comprehensive review on catalytic enantioselective aldol reactions, see: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389.
308. (b) Gröger, H.; Vogl, E. M.; Shibasaki, M. Chem. Eur. J. 1998, 4, 1137-1141.
309. Sato, M.; Sunami, S.; Sugita, Y.; Kaneko, C. Chem. Pharm. Bull. 1994, 42, 839-845.
310. Sato, M.; Sunami, S.; Sugita, Y.; Kaneko, C. Heterocycles 1995, 41, 1435-1444.
311. Singer, R. A.; Carreira, E. M. J. Am. Chem. Soc. 1995, 117, 12360-12361.
312. Dritz, J. H.; Carreira, E. M. Tetrahedron Lett. 1997, 38, 5579-5582.
313. Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837-838.
314. (a) Krüger, J.; Carreira, E. M. Tetrahedron Lett. 1998, 39, 7013-7016.
315. See also: (b) Casiraghi, G.; Zanardi, F.; Appendino, G. ChemTracts-Org. Chem. 1999, 12, 695-702.
316. The mechanism of these Cu-catalyzed asymmetric aldol reactions was recently studied by Carreira, who postulated a catalytic cycle with the involvement of metalloenolate and metal aldolate intermediates: Pagenkopf, B. L.; Krüger, J.; Stojanovic, A.; Carreira, E. M. Angew. Chem., Int. Ed. Engl. 1998, 37, 3124-3126.
317. Evans, D. A.; Kozlowski, M. C.; Murry, J. A.; Burgey, C. S.; Campos, K. R.; Connell, B. T.; Staples, R. J. J. Am. Chem. Soc. 1999, 121, 669-685.
318. Evans, D. A.; Burgey, C. S.; Kozlowski, M. C.; Tregay, S. W. J. Am. Chem. Soc. 1999, 121, 686-699.
319. Anné, S.; Yong, W.; Vandewalle, M. Synthesis 1999, 1435-1437.
320. Soriente, A.; De Rosa, M.; Dovinola, P.; Sodano, G.; Scettri, A. Tetrahedron: Asymmetry 1998, 9, 2197-2199.
321. Szlosek, M.; Franck, X.; Figadère, B.; Cavé, A. J. Org. Chem. 1998, 63, 5169-5172.
322. Pichon, M.; Jullian, J.-C.; Figadère, B.; Cavé, A. Tetrahedron Lett. 1998, 39, 1755-1758.