The Reformatsky reaction in organic synthesis. Recent advances

Tetrahedron

Volumn 60, Issue 42, 2004, Pages 9325-9374

  Ocampo, Rogelio ^a   Dolbier Jr , William R ^b  

^a UNIVERSIDAD DE CALDAS   (Colombia)

^b Gainesville FL 32611 7200 USA ^*  (United States)

Author keywords

Organic synthesis; Organozinc reagent; Reformatsky reaction

Indexed keywords

ACRYLIC ACID DERIVATIVE; AMIDE; CARBON; CARBONYL DERIVATIVE; CHROMIUM; CROTONIC ACID DERIVATIVE; HALOGEN; INDIUM; METAL; METHYL GROUP; ORGANIC COMPOUND; REAGENT; SAMARIUM DIIODIDE; ZINC;

ATOM; CATALYSIS; CATALYST; CHIRALITY; FLUORINATION; MICHAEL ADDITION; MOLECULE; PRIORITY JOURNAL; REFORMATSKY REACTION; REVIEW; STEREOCHEMISTRY; SYNTHESIS;

EID: 4544347622     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.07.018     Document Type: Review

References (467)

1. S. Reformatsky Ber. Dtsch. Chem. Ges. 20 1887 1210
2. F. Orsini, and G. Sello Curr. Org. Synth. 1 2004 111 135
3. A. Fürstner Synthesis 1989 571 590
4. (a) Fürstner, A. In Encyclopedia of Reagents for Organic Synthesis. Paquette, L. A., Ed.; Wiley: New York, 1995; pp 2402-2408.
5. (b) Fürstner, A. In Organozinc Reagents. Knochel, P., Jones, P., Eds.; University Press: Oxford, 1999; pp 287-305.
6. (c) Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis. Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 277-299.
7. (d) Rathke, M. W. In Organic Reactions. John Wiley and Sons: New York, 1975; Vol. 22, Chapter 2, pp 30-59.
8. Zinc-induced Reformatsky reactions should be considered only a small subdivision of organozinc chemistry. (a). For documentation on organozinc chemistry, see: Organozine Reagents. Knochel, P., Jones, P., Eds.; University Press: Oxford, 1999; 354 p For a review on transition metal catalyzed reactions of organozinc reagents, see: E. Erdik Tetrahedron 48 1992 9577 9648
9. Zinc-induced Reformatsky reactions should be considered only a small subdivision of organozinc chemistry. (a). For documentation on organozinc chemistry, see: Organozine Reagents. Knochel, P., Jones, P., Eds.; University Press: Oxford, 1999; 354 p For a review on transition metal catalyzed reactions of organozinc reagents, see: E. Erdik Tetrahedron 48 1992 9577 9648
10. M.C.C. Areias, L.W. Bieber, M. Navarro, and F.B. Diniz J. Electroanal. Chem. 558 2003 125 130
11. W. Horner, and H. Bertagnolli J. Organomet. Chem. 649 2002 128 135
12. T.S. Ertel, W. Horner, I. Abraham, and H. Bertagnolli J. Phys. IV 7 1997 947 948
13. For older reviews, see: (a) Shriner, R. L. Org. React. 1942, 1, 1. (b) Rathke, M. W. Org. React. 1975, 22, 423-460. (c) Gaudemar, M. Organomet. Chem. Rev., Sect. A, 1972, 8, 183-233. (d) Nützel, K. Houben-Weyl, Vol. XIII/2a, Georg Thieme: Stuttgart, 1973, p 805. (e) Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89. (f) Brossi, M.; Kaenel, H. R. Schweiz. Lab.-Z, 1984, 41, 55-57. (g) Vul'fson, N. S.; Vinograd. L. K. Reactions and Research Methods for Organic Compounds Reformatsky Reaction, Vol. 17; Khimiya: Moscow, 1967.
14. For older reviews, see: (a) Shriner, R. L. Org. React. 1942, 1, 1. (b) Rathke, M. W. Org. React. 1975, 22, 423-460. (c) Gaudemar, M. Organomet. Chem. Rev., Sect. A, 1972, 8, 183-233. (d) Nützel, K. Houben-Weyl, Vol. XIII/2a, Georg Thieme: Stuttgart, 1973, p 805. (e) Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89. (f) Brossi, M.; Kaenel, H. R. Schweiz. Lab.-Z, 1984, 41, 55-57. (g) Vul'fson, N. S.; Vinograd. L. K. Reactions and Research Methods for Organic Compounds Reformatsky Reaction, Vol. 17; Khimiya: Moscow, 1967.
15. For older reviews, see: (a) Shriner, R. L. Org. React. 1942, 1, 1. (b) Rathke, M. W. Org. React. 1975, 22, 423-460. (c) Gaudemar, M. Organomet. Chem. Rev., Sect. A, 1972, 8, 183-233. (d) Nützel, K. Houben-Weyl, Vol. XIII/2a, Georg Thieme: Stuttgart, 1973, p 805. (e) Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89. (f) Brossi, M.; Kaenel, H. R. Schweiz. Lab.-Z, 1984, 41, 55-57. (g) Vul'fson, N. S.; Vinograd. L. K. Reactions and Research Methods for Organic Compounds Reformatsky Reaction, Vol. 17; Khimiya: Moscow, 1967.
16. For older reviews, see: (a) Shriner, R. L. Org. React. 1942, 1, 1. (b) Rathke, M. W. Org. React. 1975, 22, 423-460. (c) Gaudemar, M. Organomet. Chem. Rev., Sect. A, 1972, 8, 183-233. (d) Nützel, K. Houben-Weyl, Vol. XIII/2a, Georg Thieme: Stuttgart, 1973, p 805. (e) Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89. (f) Brossi, M.; Kaenel, H. R. Schweiz. Lab.-Z, 1984, 41, 55-57. (g) Vul'fson, N. S.; Vinograd. L. K. Reactions and Research Methods for Organic Compounds Reformatsky Reaction, Vol. 17; Khimiya: Moscow, 1967.
17. For older reviews, see: (a) Shriner, R. L. Org. React. 1942, 1, 1. (b) Rathke, M. W. Org. React. 1975, 22, 423-460. (c) Gaudemar, M. Organomet. Chem. Rev., Sect. A, 1972, 8, 183-233. (d) Nützel, K. Houben-Weyl, Vol. XIII/2a, Georg Thieme: Stuttgart, 1973, p 805. (e) Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89. (f) Brossi, M.; Kaenel, H. R. Schweiz. Lab.-Z, 1984, 41, 55-57. (g) Vul'fson, N. S.; Vinograd. L. K. Reactions and Research Methods for Organic Compounds Reformatsky Reaction, Vol. 17; Khimiya: Moscow, 1967.
18. For older reviews, see: (a) Shriner, R. L. Org. React. 1942, 1, 1. (b) Rathke, M. W. Org. React. 1975, 22, 423-460. (c) Gaudemar, M. Organomet. Chem. Rev., Sect. A, 1972, 8, 183-233. (d) Nützel, K. Houben-Weyl, Vol. XIII/2a, Georg Thieme: Stuttgart, 1973, p 805. (e) Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89. (f) Brossi, M.; Kaenel, H. R. Schweiz. Lab.-Z, 1984, 41, 55-57. (g) Vul'fson, N. S.; Vinograd. L. K. Reactions and Research Methods for Organic Compounds Reformatsky Reaction, Vol. 17; Khimiya: Moscow, 1967.
19. For older reviews, see: (a) Shriner, R. L. Org. React. 1942, 1, 1. (b) Rathke, M. W. Org. React. 1975, 22, 423-460. (c) Gaudemar, M. Organomet. Chem. Rev., Sect. A, 1972, 8, 183-233. (d) Nützel, K. Houben-Weyl, Vol. XIII/2a, Georg Thieme: Stuttgart, 1973, p 805. (e) Diaper, D. G. M.; Kuksis, A. Chem. Rev. 1959, 59, 89. (f) Brossi, M.; Kaenel, H. R. Schweiz. Lab.-Z, 1984, 41, 55-57. (g) Vul'fson, N. S.; Vinograd. L. K. Reactions and Research Methods for Organic Compounds Reformatsky Reaction, Vol. 17; Khimiya: Moscow, 1967.
20. M.-X. Zhao, M.-X. Wang, C.-Y. Yu, Z.-T. Huang, and G.W. Fleet J. Org. Chem. 69 2004 997 1000
21. M.P. Bowman, J.P.G. Senet, T. Malfroot, and R.A. Olofson J. Org. Chem. 55 1990 5982 5986
22. V.V. Shchepin, N.Y. Russkikh, and D.A. Desyatkov Zh. Org. Khim. 29 1993 2316 2317
23. V.V. Shchepin, T.Y. Chuprikova, and I.Y. Petukhova Zh. Org. Khim. 27 1991 1796 1797
24. V.V. Shchepin, D.I. Efremov, and D.A. Desyatkov Zh. Org. Khim. 29 1993 410 411
25. For a review on some aspects on the stereochemistry of the Reformatsky reactions, see: Guette, J. P. In Organomettaliques Fonct. Ambidents, Recl. Commun., Colloq. Fr.-Bulg.; Blagoev, B., Gaudemar-Bardone, F., Mladenova, M., Eds., 1980. Acad. Bulg. Sci., Inst. Chim. Org.: Sofia, pp 123-129.
26. For a review on some aspects on the stereochemistry of the Reformatsky reactions, see: Guette, J. P. In Organomettaliques Fonct. Ambidents, Recl. Commun., Colloq. Fr.-Bulg.; Blagoev, B., Gaudemar-Bardone, F., Mladenova, M., Eds., 1980. Acad. Bulg. Sci., Inst. Chim. Org.: Sofia, pp 123-129.
27. H. Akita, S.-Y. Chen, and S. Nagumo Tetrahedron: Asymmetry 5 1994 1207 1210
28. J.I. DeGraw, P.H. Christie, R.L. Kisliuk, Y. Gaumont, and F.M. Sirotnak J. Med. Chem. 33 1990 212 215
29. R.H. Khan, and R.C. Rastogi Indian J. Chem. Sect. B 31B 1992 276
30. S. Witkowski, Y.K. Rao, R.H. Premchandran, P.V. Halushka, and J. Fried J. Am. Chem. Soc. 114 1992 8464 8472
31. M. Gomes Constantino, L. Gonzaga de Oliveira Matias, G.V.J. da Silva, V.C. Gomes Heleno, and M.T.D.P. Gambardella Synth. Commun. 27 1997 4285 4295
32. I. Izquierdo, M.T. Plaza, R. Robles, A.J. Mota, and F. Franco Tetrahedron: Asymmetry 12 2001 2749 2754
33. J.K. Gawronski Tetrahedron Lett. 25 1984 2605
34. G. Picotin, and P. Miginiac J. Org. Chem. 52 1987 4796
35. C.J. Stephen Tetrahedron Lett. 33 1992 6193 6196
36. S. Guertler, S. Ruf, M. Johner, and H.H. Otto Pharmazie 51 1996 811 815
37. M. Gaudemar Tetrahedron Lett. 24 1983 2749
38. I. Kuwajima, E. Nakamura, and K. Hashimoto Org. Synth. 61 1983 122
39. G.E. Stocker, W.F. Hoffmann, A.W. Alberts, E.J. Cragoe, A.A. Peana, J.L. Gilfillan, J.W. Huff, F.C. Novello, J.D. Prugh, R.L. Smith, and A.K. Willard J. Med. Chem. 28 1985 347
40. K. Maruoka, S. Hashimoto, Y. Kitagawa, H. Yamamoto, and H. Nozaki Bull. Chem. Soc. Jpn 53 1980 3301
41. K. Maruoka, S. Hashimoto, Y. Kitagawa, H. Yamamoto, and H. Nozaki J. Am. Chem. Soc. 99 1977 7705
42. M. Kuroboshi, and T. Ishihara Tetrahedron Lett. 28 1987 6481
43. T. Ishihara, and M. Kuroboshi Chem. Lett. 1987 1145
44. M. Bellasoued, R. Arous-Chtara, and M. Gaudemar J. Organomet. Chem. 231 1982 185
45. M. Lucas, and J.P. Guetté J. Chem. Res. (S) 1978 214
46. M. Bellasoued, and M. Gaudemar J. Organomet. Chem. 93 1975 9
47. F. Gaudemar-Bardone, M. Gaudemar, and M. Mladenova Synthesis 1987 1130
48. M. Bogavac, L. Arsenijevic, and V. Arsenijevic Bull. Soc. Chim. Fr. II 1980 145
49. E. Santaniello, and A. Manzocchi Synthesis 1977 698
50. N. Slougui, and G. Rousseau Synth. Commun. 17 1987 1
51. R. Csuk, A. Fürstner, and H. Weidmann J. Chem. Soc., Chem. Commun. 1986 775
52. R. Csuk, and B.I. Glaenzer J. Carbohydr. Chem. 9 1990 797 807
53. R.D. Rieke, P.T.J. Li, T.P. Burns, and S.T. Uhm J. Org. Chem. 46 1981 4323
54. P. Boudjouk, D.P. Thompson, W.H. Ohrbom, and B.H. Han Organometallics 5 1986 1257
55. R.D. Rieke, and S.J. Uhm Synthesis 1975 452
56. R.T. Arnold, and S.T. Kulenovic Synth. Commun. 7 1977 223
57. M. Makosza, K. Grela, and W. Fabianowski Tetrahedron 52 1996 9575 9580
58. S. Malfait, L. Pélinski, and J. Brocard Tetrahedron: Asymmetry 9 1998 2595 2610
59. Y. Ukaji, Y. Yoshida, and K. Inomata Tetrahedron: Asymmetry 11 2000 733 736
60. Y. Aoyagi, W. Tanaka, and A. Ohta J. Chem. Soc., Chem. Commun. 1994 1225 1226
61. Y. Kataoka, I. Makihira, T. Yamagata, and K. Tani Organometallics 16 1997 4788 4795
62. T.T. Curran J. Org. Chem. 58 1993 6360 6363
63. Z. Zhao, Y. Ding, and G. Zhao Synth. Commun. 31 2001 2089 2096
64. Y. Ding, Z. Zhao, and C. Zhow Tetrahedron 53 1997 2899 2906
65. V.I. Fylyakova, F.G. Saitkulova, and K.I. Pashkevich Izv. Akad. Nauk. Ser. Khim. 1992 1228 1229
66. Y. Horiuchi, M. Taniguchi, K. Oshima, and K. Utimoto Tetrahedron Lett. 36 1995 5353 5356
67. T. Basile, E. Tagliavini, C. Trombini, and A. Umani-Ronchi Synthesis 1990 305 311
68. A. Chattopadhyay, and A. Salaskar Synthesis 2000 561 564
69. K. Nozaki, K. Oshima, and K. Utimoto Bull. Chem. Soc. Jpn 64 1991 403 409
70. Y. Shen, and M. Qi J. Fluorine Chem. 67 1994 229 232
71. Y. Shen, and M. Qi J. Chem. Res. (S) 1993 222 223
72. R. Ocampo, W.R. Dolbier Jr., K.A. Abboud, and F. Zuluaga J. Org. Chem. 67 2002 72 78
73. A. Kagayama, K. Igarashi, I. Shiina, and T. Mukaiyama Bull. Chem. Soc. Jpn 73 2000 2579 2585
74. T. Mukaiyama, A. Kagayama, K. Igarashi, and I. Shiina Chem. Lett. 1999 1157 1158
75. M. Hayashi, M. Sugiyama, T. Toba, and N. Oguni J. Chem. Soc., Chem. Commun. 1990 767 768
76. Y. Hashimoto, and S. Kikuchi Chem. Lett. 2002 126 127
77. M. Shimizu, F. Kobayashi, and R. Hayakawa Tetrahedron 57 2001 9591 9595
78. J.D. Parrish, D.R. Shelton, and R.D. Little Org. Lett. 5 2003 3615 3617
79. J.D. Parrish, D.R. Shelton, Y.S. Park, and R.D. Little Proc. Electrochem. Soc. 2003-12 2003 161 164
80. M. Sánchez, and F. Bermejo Tetrahedron Lett. 38 1997 5057 5060
81. S. Kim, W.S. Han, and J.M. Lee Bull. Kor. Chem. Soc. 13 1992 466 467
82. A.R. Katritzky, D.A. Nichols, and M. Qi Tetrahedron Lett. 39 1998 7063 7066
83. A. Vidal, A. Nefzi, and R.A. Houghten J. Org. Chem. 66 2001 8268 8272. Vidal, A.; Nefzi, A.; Houghten, R. A. Abstr. Pap., 223rd ACS National Meeting, 2002, ORGN-234 and FLUO-008.
84. A. Vidal, A. Nefzi, and R.A. Houghten J. Org. Chem. 66 2001 8268 8272. Vidal, A.; Nefzi, A.; Houghten, R. A. Abstr. Pap., 223rd ACS National Meeting, 2002, ORGN-234 and FLUO-008.
85. Katritzky, A. R.; Hong, Q.; Yang, Z. J. Org. Chem. 1995, 60, 3405-3408.
86. (b) Strah, S.; Katritzky, A. R.; Belyakov, S. A. Abstr. Pap.-Am. Chem. Soc. 1998, 215th ORGN-191.
87. For a recent review on chromium (II) and chromium (III)-mediated organic synthesis, included the chromium-Reformatsky reaction, see: (a) A. Fürstner Chem. Rev. 99 1999 991 1045
88. L.A. Wessjohann, and G. Scheid Synthesis 1 1999 1 36
89. For reviews on the application of SmI2 in organic synthesis, see: (a) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345. (e) Molander, G. A. In Organic Reactions; Paquette, L. A., Ed. John Wiley: New York, 1994, Vol. 46, p 211. (f) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994. (g) Molander, G. A. Chem. Rev. 1992, 92, 29. (h) Curran, D. P.; Fevig, T. L.; Jaspersen, C. P.; Totleben, M. L. Synlett 1992, 943. (i) Inanaga, J. Trends Org. Chem. 1990, 1, 23-30.
90. For reviews on the application of SmI2 in organic synthesis, see: (a) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345. (e) Molander, G. A. In Organic Reactions; Paquette, L. A., Ed. John Wiley: New York, 1994, Vol. 46, p 211. (f) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994. (g) Molander, G. A. Chem. Rev. 1992, 92, 29. (h) Curran, D. P.; Fevig, T. L.; Jaspersen, C. P.; Totleben, M. L. Synlett 1992, 943. (i) Inanaga, J. Trends Org. Chem. 1990, 1, 23-30.
91. For reviews on the application of SmI2 in organic synthesis, see: (a) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345. (e) Molander, G. A. In Organic Reactions; Paquette, L. A., Ed. John Wiley: New York, 1994, Vol. 46, p 211. (f) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994. (g) Molander, G. A. Chem. Rev. 1992, 92, 29. (h) Curran, D. P.; Fevig, T. L.; Jaspersen, C. P.; Totleben, M. L. Synlett 1992, 943. (i) Inanaga, J. Trends Org. Chem. 1990, 1, 23-30.
92. For reviews on the application of SmI2 in organic synthesis, see: (a) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345. (e) Molander, G. A. In Organic Reactions; Paquette, L. A., Ed. John Wiley: New York, 1994, Vol. 46, p 211. (f) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994. (g) Molander, G. A. Chem. Rev. 1992, 92, 29. (h) Curran, D. P.; Fevig, T. L.; Jaspersen, C. P.; Totleben, M. L. Synlett 1992, 943. (i) Inanaga, J. Trends Org. Chem. 1990, 1, 23-30.
93. For reviews on the application of SmI2 in organic synthesis, see: (a) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345. (e) Molander, G. A. In Organic Reactions; Paquette, L. A., Ed. John Wiley: New York, 1994, Vol. 46, p 211. (f) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994. (g) Molander, G. A. Chem. Rev. 1992, 92, 29. (h) Curran, D. P.; Fevig, T. L.; Jaspersen, C. P.; Totleben, M. L. Synlett 1992, 943. (i) Inanaga, J. Trends Org. Chem. 1990, 1, 23-30.
94. For reviews on the application of SmI2 in organic synthesis, see: (a) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345. (e) Molander, G. A. In Organic Reactions; Paquette, L. A., Ed. John Wiley: New York, 1994, Vol. 46, p 211. (f) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994. (g) Molander, G. A. Chem. Rev. 1992, 92, 29. (h) Curran, D. P.; Fevig, T. L.; Jaspersen, C. P.; Totleben, M. L. Synlett 1992, 943. (i) Inanaga, J. Trends Org. Chem. 1990, 1, 23-30.
95. For reviews on the application of SmI2 in organic synthesis, see: (a) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345. (e) Molander, G. A. In Organic Reactions; Paquette, L. A., Ed. John Wiley: New York, 1994, Vol. 46, p 211. (f) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994. (g) Molander, G. A. Chem. Rev. 1992, 92, 29. (h) Curran, D. P.; Fevig, T. L.; Jaspersen, C. P.; Totleben, M. L. Synlett 1992, 943. (i) Inanaga, J. Trends Org. Chem. 1990, 1, 23-30.
96. For reviews on the application of SmI2 in organic synthesis, see: (a) Krief, A.; Laval, A.-M. Chem. Rev. 1999, 99, 745. (b) Molander, G. A.; Harris, C. R. Chem. Rev. 1996, 96, 307. (c) Molander, G. A.; Harris, C. R. Tetrahedron 1998, 54, 3321. (d) Skrydstrup, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 345. (e) Molander, G. A. In Organic Reactions; Paquette, L. A., Ed. John Wiley: New York, 1994, Vol. 46, p 211. (f) Imamoto, T. Lanthanides in Organic Synthesis; Academic Press: London, 1994. (g) Molander, G. A. Chem. Rev. 1992, 92, 29. (h) Curran, D. P.; Fevig, T. L.; Jaspersen, C. P.; Totleben, M. L. Synlett 1992, 943. (i) Inanaga, J. Trends Org. Chem. 1990, 1, 23-30.
97. For reviews on indium in organic synthesis, see: (a) J. Podlech, and T.C. Maier Synthesis 2003 633. (b) P. Cintas Synlett 1995 1087
98. For reviews on indium in organic synthesis, see: (a) J. Podlech, and T.C. Maier Synthesis 2003 633. (b) P. Cintas Synlett 1995 1087
99. L.A. Wessjohann, and H. Wild Synthesis 1997 512 514
100. L.A. Wessjohann, and H. Wild Synlett 6 1997 731 733
101. C.T. Buse, and C.H. Heathcock Tetrahedron Lett. 19 1978 1685
102. J. Mainz, A. Arrieta, X. Lopez, J.M. Ugalde, F.P. Cossio, and B. Lecea Tetrahedron Lett. 34 1993 6111 6114
103. L.A. Wessjohann, and H. Wild Synlett 1997 731
104. T. Gabriel, and L.A. Wessjohann Tetrahedron Lett. 38 1997 1363 1366
105. T. Gabriel, and L.A. Wessjohann Tetrahedron Lett. 38 1997 4387 4388
106. L.A. Wessjohann, and T. Gabriel J. Org. Chem. 62 1997 3772 3774
107. R. Wittenberg, C. Beier, G. Drager, G. Jas, C. Jasper, H. Monenschein, and A. Kirschning Tetrahedron Lett. 45 2004 4457 4460
108. H.S. Park, I.S. Lee, and Y.H. Kim Tetrahedron Lett. 36 1995 1673 1674
109. S. Fukuzawa, K. Mutoh, T. Tsuchimoto, and T. Hiyama J. Org. Chem. 61 1996 5400 5405
110. X.L. Xu, P. Lu, and Y.-M. Zhang Chin. Chem. Lett. 10 1999 729 730
111. J.-M. Zhang, and Y.-M. Zhang Chin. J. Chem. 20 2002 111 113
112. K. Hirano, and S. Fukuzawa Kidorui 32 1998 312 313
113. S. Fukuzawa, and K. Hirai J. Chem. Soc., Perkin Trans. 1 1993 1963 1965
114. M.I. Lannou, F. Helion, and J.-L. Namy Tetrahedron 59 2003 10551 10565
115. Chauhan, K. K.; Frost, C. G.; Waite, D. C. Abstr. Pap.-220th ACS Meeting, 2000, ORGN-114.
116. Z. Wang, and G.B. Hammond J. Org. Chem. 65 2000 6547
117. P.S. Johar, S. Araki, and Y. Butsugan J. Chem. Soc., Perkin Trans. 1 1992 711 713
118. K. Bang, K. Lee, Y.K. Park, and P.H. Lee Bull. Kor. Chem. Soc. 23 2002 1272 1276
119. P.H. Lee, K. Bang, K. Lee, S.-Y. Sung, and S. Chang Synth. Commun. 31 2001 3781 3789
120. W.J. Chung, S. Higashiya, and J.T. Welch J. Fluorine Chem. 112 2001 343 347
121. Banik, B. K.; Ghatak, A.; Becker, F. F. Abstr. Pap., 223rd ACS National Meeting, 2002, ORGN-308.
122. I. Izquierdo, M.T. Plaza, J.A. Tamayo, and A.J. Mota Synthesis 2004 1083 1087
123. S. Araki, N. Katsumura, K. Kawasaki, and Y. Butsugan J. Chem. Soc., Perkin Trans. 1 1991 499 500
124. H. Schick, R. Ludwig, K.-H. Schwarz, K. Kleiner, and A. Kunath J. Org. Chem. 59 1994 3161 3164
125. H. Schick, R. Ludwig, K. Kleiner, and A. Kunath Tetrahedron 51 1995 2939 2946
126. K.-H. Schwarz, K. Kleiner, R. Ludwig, and H. Schick J. Org. Chem. 57 1992 4013 4015
127. K.-H. Schwarz, K. Kleiner, R. Ludwig, and H. Schick Chem. Ber. 126 1993 1247 1249
128. M. Durandetti, C. Meignein, and J. Perichon Org. Lett. 5 2003 317 320
129. L. Tussa, C. Lebreton, and P. Mosset Chem.-A Eur. J. 3 1997 1064 1070
130. T. Hirashita, K. Kinoshita, H. Yamamura, M. Kawai, and S. Araki J. Chem. Soc., Perkin Trans. 1 2000 825 828
131. A. Conan, S. Sibille, and J. Perichon J. Org. Chem. 56 1991 2018 2024
132. S. Mcharek, S. Sibille, J.Y. Nedelec, and J. Perichon J. Organomet. Chem. 401 1991 211 215
133. Z. Shen, J. Zhang, H. Zou, and M. Yang Tetrahedron Lett. 38 1997 2733 2736
134. H. Kagoshima, Y. Hashimoto, and K. Saigo Tetrahedron Lett. 39 1998 8465 8466
135. Y. Han, Z.-F. Chi, and Y.Z. Huang Chin. Chem. Lett. 7 1996 713 716
136. H. Kagoshima, Y. Hashimoto, D. Oguro, and K. Saigo J. Org. Chem. 63 1998 691 697
137. H. Kagoshima, Y. Hashimoto, D. Oguro, T. Kutsuna, and K. Saigo Tetrahedron Lett. 39 1998 1203 1206
138. (a) Orsini, F.; Pelizzoni, T.; Pulici, M.; Vallarino, L. M. J. Org. Chem. 1994, 59, 1-3.
139. (b) Orsini, F. J. Org. Chem. 1997, 62, 1159.
140. (c) Orsini, F.; Pulici, M. In Trends in Organometallic Chemistry, Research Trends Ed., Trivandrum: India, 1994; Vol. 1, pp 625-667.
141. (d) Orsini, F.; Pulici, M.; Vallarino, L. M. J. Organomet. Chem. 1995, 495, C1-C5.
142. F. Orsini Tetrahedron Lett. 39 1998 1425 1428
143. F. Orsini, and C. Leccioli Tetrahedron: Asymmetry 8 1997 4011 4019
144. G.R. Pettit, and M.P. Grealish J. Org. Chem. 66 2001 8640 8642
145. J.J. Duffield, and G.R. Pettit J. Nat. Prod. 64 2001 472 479
146. K. Kanai, H. Wakabayashi, and T. Honda Org. Lett. 2 2000 2549 2551
147. J.A. Marshall Chemtracts 13 2000 705 707
148. T. Honda, H. Wakabayashi, and K. Kanai Chem. Pharm. Bull. 50 2002 307 308
149. Review: R. Csuk, B.I. Glänzer, and A. Fürstner Adv. Organomet. Chem. 28 1988 85 137
150. R. Csuk, C. Schröeder, and C. Krieger Tetrahedron 53 1997 12947 12960
151. S. Hanessian, and C. Girard Synlett 1994 865 867
152. Y. Yokoyama, T. Tsuchikawa, M. Hiramatsu, and K. Mochida Main Group Metal Chem. 23 2000 691 693
153. K. Takai, T. Ueda, T. Hayashi, and T. Moriwake Tetrahedron Lett. 37 1996 7049 7052
154. Y.-S. Suh, and R.D. Rieke Tetrahedron Lett. 45 2004 1807 1809
155. K. Takai, T. Kakiuchi, and K. Utimoto J. Org. Chem. 59 1994 2671 2673
156. A. Fürstner, and A. Hupperts J. Am. Chem. Soc. 117 1995 4468 4475
157. P. Knochel, M.C.P. Yeh, S.C. Berk, and J. Talbert J. Org. Chem. 53 1988 2390 2392
158. M. Gaudemar Bull. Soc. Chim. Fr. 1962 974 987
159. H. Kakiya, S. Nishimae, H. Shinokubo, and K. Oshima Tetrahedron 57 2001 8807 8815
160. A.S. Demir, C. Tanyeli, A.S. Mahasneh, and H. Aksoy Synthesis 1994 155 157
161. S.G. Davies, A.J. Edwards, G.B. Evans, and A.A. Mortlock Tetrahedron 50 1994 6621 6642
162. I. Shibata, T. Yamaguchi, A. Baba, and H. Matsuda Chem. Lett. 1993 97 100
163. I. Shibata, T. Suwa, H. Sakakibara, and A. Baba Org. Lett. 4 2002 301 303
164. N.Y. Kuznetsov, V.N. Khrustalev, A.B. Terentiev, and Y.N.A.N. Belokon Russ. Chem. Bull. 50 2001 548 550
165. A.B. Terent'ev, T.T. Vasil'eva, N.A. Kuz'mina, O.V. Chakhovskaya, E.S. Brodsky, and Y.N. Belokon' Russ. Chem. Bull. 49 2000 722 723
166. A.B. Terent'ev, T.T. Vasil'eva, N.A. Kuz'mina, E.I. Mysov, N.S. Ikonnikov, N.Y. Kuznetsov, and Y.N. Belokon' Russ. Chem. Bull. 48 1999 1121 1127
167. A.B. Terentiev, T.T. Vasilieva, N.A. Kuzmina, E.I. Mysov, N.Y. Kuznetzov, and Y.N. Belokon J. Chem. Res. (S) 1998 306 [J. Chem. Res. (M) 1998, 1281-9]
168. C.D. Roberts, R. Schutz, and C.J. Leumann Synlett 6 1999 819 821
169. M. Cantin, R. Schutz, and C.J. Leumann Tetrahedron Lett. 38 1997 4211 4214
170. E. De Vos, E.L. Esmans, F.C. Alderweireldt, J. Balzarini, and E. De Clercq J. Heterocycl. Chem. 30 1993 1245 1252
171. A. Yanagisawa, H. Takahashi, and T. Arai Chem. Commun. 2004 580 581
172. For a review on non-conventional reaction conditions (ultrasound, high pressure and microwave heating) in organic synthesis, see: R.J. Giguere Org. Synth.: Theory Appl. 1 1989 103 172
173. For a review on solvent-free reactions, see: K. Tanaka, and F. Toda Chem. Rev. 100 2000 1025 1074
174. For a review on water medium, see: C.J. Li Chem. Rev. 93 1993 2023
175. A.R. Gholap, and A.P. Chavan J. Chem. Res. (S) 2003 374 376
176. K. Tanaka, S. Kishigami, and F. Toda J. Org. Chem. 56 1991 4333 4334
177. R. Latouche, F. Texier-Boullet, and J. Hamelin Bull. Soc. Chim. Fr. 130 1993 535 546
178. R. Latouche, F. Texier-Boullet, and J. Hamelin Tetrahedron Lett. 32 1991 1179 1182
179. G.-W. Wang, Y. Murata, K. Komatsu, and T.S.M. Wan Chem. Commun. 1996 2059 2060
180. Wang, Z.; Meier, M. S. Abstr. Pap.-223rd ACS Meeting 2002, ORGN-134.
181. D.J. Dellinger, D.M. Sheehan, N.K. Christensen, J.G. Lindberg, and M.H. Caruthers J. Am. Chem. Soc. 125 2003 940 950
182. L.W. Bieber, I. Malvestiti, and C. Storch J. Org. Chem. 62 1997 9061 9064
183. Y. Rollin, C. Gebehenne, S. Derien, E. Dunach, and J. Perichon J. Organomet. Chem. 461 1993 9 13
184. J.C. Adrian Jr., and M.L. Snapper J. Org. Chem. 68 2003 2143 2150
185. Hilgers, G.; Hess, J. Ger. Offen. German Patent: DE 90-4016076 9900518, 1991, 6 pp.
186. C.L. Lim, and B.H. Han J. Kor. Chem. Soc. 35 1991 762 764
187. N.A. Ross, and R.A. Bartsch J. Org. Chem. 68 2003 360 366
188. N.A. Ross, R.A. Bartsch, and A.P. Marchand ARKIVOC 2003 27 30
189. N.A. Ross, R.R. MacGregor, and R.A. Bartsch Tetrahedron 60 2004 2035 2041
190. T. Kitazume Ultrasonics 28 1990 322 325
191. C. Baldoli, P. Del Buttero, E. Licandro, and A. Papagni Tetrahedron 52 1996 4849 4856
192. P.L. Coe, M. Löhr, and C. Rochin J. Chem. Soc., Perkin Trans. 1 1998 2803 2812
193. J.M. Andrés, M.A. Martinez, R. Pedrosa, and A. Perez-Encabo Synthesis 1996 1070 1072
194. J.M. Altenburger, and D. Schirlin Tetrahedron Lett. 32 1991 7255 7258
195. (a) N.A. Ross, and R.A. Bartsch J. Heterocycl. Chem. 38 2001 1255 1258
196. (b) Ross, N. A.; Bartsch, R. A. Abstr. Pap.-Am. Chem. Soc. 2002, 224th ORGN-888.
197. A. Durant, J.L. Delplancke, V. Libert, and J. Reisse Eur. J. Org. Chem. 1999 2845 2851
198. M. Makosza, P. Nieczypor, and K. Grela Tetrahedron 54 1998 10827 10836
199. B.L. Mylari, and W.J. Zembrowki J. Org. Chem. 56 1991 2587 2589
200. C. Andrés, A. González, R. Pedrosa, and A. Perez-Encabo Tetrahedron Lett. 33 1992 2895 2898
201. K. Bott Tetrahedron Lett. 35 1994 555 556
202. J. Syed, S. Forster, and F. Effenberger Tetrahedron: Asymmetry 9 1998 805 815
203. J.C. Adrian, J.L. Barkin, and L. Hassib Tetrahedron Lett. 34 1999 2457 2460
204. D.A. Evans, and A.H. Hoveyda J. Am. Chem. Soc. 112 1990 6447 6449
205. T.E. Bitterwolf, and X. Dai J. Organomet. Chem. 440 1992 103 112
206. H.M.C. Ferraz, and L.F. Silva Tetrahedron 57 2001 9939 9949
207. T.A. Olugbade, R.D. Waigh, and S.P. Mackay J. Chem. Soc., Perkin Trans. 1 1990 2657 2660
208. P.O. Krasuts'kii, I.G. Semenova, O.D. Voitsits'ka, and N.V. Simurova Ukr. Khim. Zh. 63 1997 107 110
209. G.A. Olah, V.P. Reddy, J. Casanova, and G.K. Prakash J. Org. Chem. 57 1992 6431 6434
210. J.M. Andrés, R. Pedrosa, A. Pérez, and A. Pérez-Encabo Tetrahedron 57 2001 8521 8530
211. P. Yates, and M. Kaldas Can. J. Chem. 70 1992 1492 1505
212. I. Izquierdo, M.T. Plaza, R. Robles, and A. Mota Tetrahedron: Asymmetry 8 1997 2597 2606
213. J.M. Dener, L.H. Zhang, and H. Rapoport J. Org. Chem. 58 1993 1159 1166
214. J.P. Michael, C.B. de Koning, and T.V. Stanbury Tetrahedron Lett. 37 1996 9403 9406
215. J.P. Michael, G.D. Hosken, and A.S. Howard Tetrahedron 44 1988 3025 3026
216. J.P. Michael, C.B. de Koning, G.D. Hosken, and T.V. Stanbury Tetrahedron 57 2001 9635 9648
217. V.V. Shchepin, and G.E. Gladkova Zh. Org. Khim. 31 1995 1094
218. V.V. Shchepin, Y.K. Fatukhova, N.T. Kirillov, N.Y. Russkikh, and D.N. Litvinov Russ. J. Org. Chem. 36 2000 1120 1123
219. Y. Ito, and S. Terashima Tetrahedron 47 1991 2821 2834
220. Y. Ito, A. Sasaki, K. Tamoto, M. Sunagawa, and S. Terashima Tetrahedron 47 1991 2801 2820
221. Y. Kobayashi, Y. Ito, and S. Terashima Tetrahedron 48 1992 55 66
222. M. Mori, and S. Oida Bioorg. Med. Chem. Lett. 3 1993 2389 2392
223. S. Fukuzawa, H. Matsuzawa, and S. Yoshimitsu J. Org. Chem. 65 2000 1702 1706
224. S. Fukuzawa, M. Tatsuzawa, and K. Hirano Tetrahedron Lett. 39 1998 6899 6900
225. M. Seki, K. Kondo, and T. Iwasaki J. Chem. Soc., Perkin Trans. 1 1996 2851 2856
226. K. Kondo, M. Seki, T. Kuroda, T. Yamanaka, and T. Iwasaki J. Org. Chem. 60 1995 1096 1097
227. K. Kondo, M. Seki, T. Kuroda, T. Yamanaka, and T. Iwasaki J. Org. Chem. 62 1997 2877 2884
228. (a) D.K. Pyun, W.J. Jeong, H.J. Jung, J.H. Kim, J.S. Lee, C.H. Lee, and B.J. Kim Synlett 2001 1950 1952
229. (b) Jeong, W. J.; Pyun, D. K.; Jung, H. J.; Kim, J. H.; Lee, C. H.; Kim, B. J. Abstr. Pap.-Am. Chem. Soc. 2001, 221st ORGN-555.
230. X. Lu, Z. Xu, G. Yang, and R. Fan Org. Proc. Res. Dev. 5 2001 186 188
231. J.M. Andrés, R. Pedrosa, and A. Perez-Encabo Tetrahedron 56 2000 1217 1223
232. V.V. Shchepin, G.E. Gladkova, and N.Y. Russkikh Zh. Org. Khim. 28 1992 1156 1162
233. V.V. Shchepin, A.A. Tryastsin, R.V. Shchepin, M.M. Kalyuzhnyi, and S.B. Lewis Russ. J. Org. Chem. 37 2001 1596 1599
234. V.V. Shchepin, and G.E. Gladkova Zh. Org. Khim. 29 1993 474 479
235. For reviews, see: (a) N.H. Werstiuk Tetrahedron 39 1982 205
236. D. Hoppe Angew. Chem., Int. Ed. Engl. 23 1984 932
237. S. Fukuzawa, N. Sumimoto, T. Fujinami, and S. Sakai J. Org. Chem. 55 1990 1628 1631
238. E. Oler, K. Reininger, and U. Schmidt Angew. Chem., Int. Ed. Engl. 9 1970 457
239. A. Löfler, D. Pratt, J. Pucknat, G. Gelbard, and A.S. Dreiding Chimia 23 1969 413
240. T.M. Ikramuddeen, N. Chandrasekara, K. Ramarajan, G.L. Garrison, and K. Berlin Indian J. Chem. Sect. B 33B 1994 362 364
241. For reviews on the synthesis of α-methylene-γ-butyrolactones: (a) H.M.R. Hoffmann, and J. Rabe Angew. Chem., Int. Ed. Engl. 24 1985 94
242. P.A. Grieco Synthesis 1975 67
243. N. Petragnani, H.M.C. Feraz, and G.V.J. Silva Synthesis 1986 157
244. F. Richter, M. Bauer, C. Perez, C. Maichle-Möessmer, and M.E. Maier J. Org. Chem. 67 2002 2474 2480
245. M.E. Maier, and C. Pérez Synlett 1998 159 160
246. A.P. Rauter, M.J. Ferreira, J. Font, A. Virgili, M. Figueredo, J.A. Figueiredo, M.I. Ismael, and T.L. Canda J. Carbohydr. Chem. 14 1995 929 948
247. A.P. Rauter, J. Figueiredo, M. Ismael, T. Canda, J. Font, and M. Figueredo Tetrahedron: Asymmetry 12 2001 1131 1146
248. J.C. Kim, J.-A. Kim, Si.-H. Kim, J.I. Park, Se.-H. Kim, S.-K. Choi, and W.-W. Park Arch. Pharm. Res. 19 1996 235 239
249. J.C. Kim, J.-A. Kim, J.I. Park, S.-H. Kim, S.-H. Kim, S.-K. Choi, and W.-W. Park Arch. Pharm. Res. 20 1997 253 258
250. B.-R. Huang, K.-H. Lee, T.-L. Tseng, H.-M. Wang, C.-F. Chen, and C.-C. Tzeng Gaox. Yix. Kex. Zaz. 9 1993 707 711
251. B.-R. Huang, K.-H. Lee, L.C. Hwang, C.H. Han, Y.L. Chen, C.C. Tzeng, and C.F. Chen Zhong. Yaox. Zaz. 43 1991 447 455
252. J.C. Kim, S.-H. Kim, J.-A. Kim, S.-K. Choi, and W.-W. Park Arch. Pharm. Res. 21 1998 458 464
253. C.-C. Tzeng, K.-H. Lee, T.-C. Wang, C.-H. Han, and Y.-L. Chen Pharm. Res. 17 2000 715 719
254. C.-C. Tzeng, I.-L. Chen, Y.-L. Chen, T.-C. Wang, Y.-L. Chang, and C.-M. Teng Helv. Chim. Acta 83 2000 349 358
255. S.-L. Hsu, Y.-L. Chen, C.-C. Tzeng, K.-C. Fang, and J.-Y. Sheu Helv. Chim. Acta 84 2001 874 879
256. Y.-L. Chen, I.-L. Chen, C.-C. Tzeng, and T.-C. Wang Helv. Chim. Acta 83 2000 989 994
257. T.-C. Wang, Y.-L. Chen, C.-C. Tzeng, S.-S. Liou, W.-F. Tzeng, Y.-L. Chang, and C.-M. Teng Helv. Chim. Acta 81 1998 1038 1047
258. C.-C. Tzeng, Y.-L. Zhao, Y.-L. Chen, S.-S. Liou, T.-C. Wang, Y.-L. Chang, and C.-M. Teng Helv. Chim. Acta 80 1997 2337 2344
259. C.-C. Tzeng, Y.-L. Chen, C.-J. Wang, T.-C. Wang, Y.-L. Chang, and C.-M. Teng Helv. Chim. Acta 80 1997 1161 1168
260. T.-C. Wang, Y.-L. Chen, C.-C. Tzeng, S.-S. Liou, Y.-L. Chang, and C.-M. Teng Helv. Chim. Acta 79 1996 1620 1626
261. Y.-L. Chen, T.-C. Wang, H.-H. Lee, C.-C. Tzeng, Y.-L. Chang, and C.-M. Teng Helv. Chim. Acta 79 1996 651 657
262. Y.-L. Chen, T.-C. Wang, K.-C. Fang, N.-C. Chang, and C.-C. Tzeng Heterocycles 50 1999 453 462
263. T.-C. Wang, Y.-L. Zhao, and D.-H. Kuo Eur. J. Med. Chem. 36 2001 909 914
264. M.S. Sawant, R. Katoch, G.K. Trivedi, and U.R. Desai J. Chem. Soc., Perkin Trans. 1 1998 843 846
265. Y.A. Dembélé, C. Belaud, P. Hitchcock, and J. Villiéras Tetrahedron: Asymmetry 3 1992 351 354
266. H. Yamamoto, T. Oritani, and K. Yamashita Agric. Biol. Chem. 54 1990 1923 1929
267. H. Mastalerz, and M. Menard J. Org. Chem. 59 1994 3223 3226
268. K. Sakai, K. Takahashi, and T. Nukano Tetrahedron 48 1992 8229 8238
269. T. Mecozzi, and M. Petrini Tetrahedron Lett. 41 2000 2709 2712
270. S. Jain, R. Jain, J. Singh, and N. Anand Tetrahedron Lett. 35 1994 2951 2954
271. V.V. Shchepin, A.S. Rodygin, and M.I. Balandina Zh. Org. Khim. 27 1991 2035 2039
272. R. Csuk, and B.I. Glaenzer J. Carbohydr. Chem. 9 1990 809 822
273. A. Fürstner, G. Kollegger, and H. Weidmann J. Organomet. Chem. 414 1991 295 305
274. C. Kuroda, and K. Ito Bull. Chem. Soc. Jpn 69 1996 2297 2303
275. S. Akai, Y. Tsuzuki, S. Matsuda, S. Kitagaki, and Y. Kita J. Chem. Soc., Perkin Trans. 1 1992 2813 2820
276. S. Akai, Y. Tsuzuki, S. Matsuda, S. Kitagaki, and Y. Kita Synlett 1991 911 912
277. C. Palomo, J.M. Aizpurua, M. Concepcion Lopez, and N. Aurrekoetxea Tetrahedron Lett. 31 1990 2205 2208
278. C. Palomo, J.M. Aizpurua, and N. Aurrekoetxea Tetrahedron Lett. 31 1990 2209 2210
279. M.F. Jacobsen, M. Turks, R. Hazell, and T. Skrydstrup J. Org. Chem. 67 2002 2411 2417
280. M. Ricci, P. Blakskjr, and T. Skrydstrup J. Am. Chem. Soc. 122 2000 12413 12421
281. L.N. Dutta, M. Bhattacharyya, and A.K. Sarkar Can. J. Chem. 73 1995 1556 1562
282. V.V. Shchepin, A.E. Korzun, Y.K. Sazhneva, and A.N. Nedugov Chem. Heterocycl. Compd. 37 2001 374 375
283. V.V. Shchepin, D.V. Fotin, A.N. Nedugov, and V.V. Fotin Russ. J. Org. Chem. 38 2002 256 258
284. V.V. Shchepin, D.V. Fotin, A.N. Nedugov, V.V. Fotin, and M.I. Vakhrin Chem. Heterocycl. Compd. 37 2001 650
285. V.V. Shchepin, and N.F. Kirillov Chem. Heterocycl. Compd. 36 2000 1110 1111
286. N.F. Kirillov, and V.V. Shchepin Russ. J. Org. Chem. 37 2001 811 813
287. N.F. Kirillov, and V.V. Shchepin Russ. J. Org. Chem. 37 2001 1223 1224
288. N. Kise, H. Yamazaki, T. Mabuchi, and T. Shono Tetrahedron Lett. 35 1994 1561 1564
289. T. Nishiyama, H. Kishi, K. Kitano, and F. Yamada Bull. Chem. Soc. Jpn 67 1994 1765 1768
290. A. Alberola, M.A. Álvarez, C. Andrés, A. González, and R. Pedrosa Synthesis 1990 1057 1058
291. A. Datta, H. Ila, and H. Junjappa J. Org. Chem. 55 1990 5589 5594
292. Y. Ukaji, S. Takenaka, Y. Horita, and K. Inomata Chem. Lett. 2001 254 255
293. B.B. Shankar, M.P. Kirkup, S.W. McCombie, J.W. Clader, and A.K. Ganguly Tetrahedron Lett. 37 1996 4095 4098
294. A.J. Robinson, and P.B. Wyatt Tetrahedron 49 1993 11329 11340
295. J.-H. Lee, Y.-Y. Lee, Y.-M. Goo, and K. Kim Bull. Kor. Chem. Soc. 14 1993 172 174
296. D.J. Hart, and D.-C. HA Chem. Rev. 89 1989 1447
297. V.V. Fotin, V.V. Shchepin, D.V. Fotin, and M.I. Vakhrin Russ. J. Org. Chem. 35 1999 1278 1281
298. S.D. Lindell, and R.M. Turner Tetrahedron Lett. 31 1990 5381 5384
299. H. Schick, and R. Ludwig Synthesis 1992 369 370
300. M.-X. Wang, Y. Liu, H.-Y. Gao, Y. Zhang, C.-Y. Yu, Z.-T. Huang, and G.W.J. Fleet J. Org. Chem. 68 2003 3281 3286
301. S. Brandaenge, E. Holmgren, H. Leijonmarck, and B. Rodríguez Acta Chem. Scand. 49 1995 922 928
302. F.A. Yassin, A.F. El-Farargy, M.M. El-Mobayed, M.Y. El-Kady, and M.R. Abd El-Maksoud J. Chem. Soc. Pakist. 13 1991 267 272
303. M.A. El-Safty, S.A. El-Bahaei, and F.A. Yassin Afinidad 49 1992 131 134
304. C. Kashima, X.C. Huang, Y. Harada, and A. Hosomi J. Org. Chem. 58 1993 793 794
305. C. Kashima, I. Kita, K. Takahashi, and A. Hosomi J. Heterocycl. Chem. 32 1995 723 725
306. P. Kielbasinski, and M. Mikolajczyk Synthesis 1995 144 146
307. E. Fagadar-Cosma, and G. Fagadar-Cosma Rev. Roum. Chim. 48 2003 211 217
308. H.K. Lee, J. Kim, and C.S. Pak Tetrahedron Lett. 40 1999 2173 2174
309. J.P. Michael, C.B. de Koning, R.L. Petersen, and T.V. Stanbury Tetrahedron Lett. 42 2001 7513 7516
310. M. Chandrasekharam, L. Bhat, H. Ila, and H. Junjappa Tetrahedron Lett. 34 1993 6439 6442
311. S.M. Hannick, and Y.J. Kishi J. Org. Chem. 48 1983 3833 3835
312. K. Mohri, Y. Yoshida, S. Mataga, Y. Hisatsune, K. Isobe, and Y. Tsuda Heterocycles 45 1997 2405 2412
313. C. Dartiguelongue, S. Payan, O. Duval, L.M. Gomès, and R. Waigh Bull. Soc. Chim. Fr. 134 1997 769 772
314. J.J. Duffield, and A.C. Regan Tetrahedron: Asymmetry 7 1996 663 666
315. Poechlauer, P.; Hartmann, M.; Mayrhofer, H. Abstr. Pap.-Am. Chem. Soc. 2001, 221st ORGN-507.
316. L. Bernardi, B.F. Bonini, E. Capito, G. Dessole, M. Fochi, M. Comes-Franchini, and A. Ricci Synlett 2003 1778 1782
317. A. Sheppard, and M.J. Miller J. Chem. Soc., Perkin Trans. 1 1990 2519 2525
318. R.R. Akhmetvaleev, L.R. Imaeva, T.A. Belogaeva, I.P. Baikova, and M.S. Miftakhov Russ. J. Org. Chem. 35 1999 242 245
319. J.F. Lavallee, C. Spino, R. Ruel, K.T. Hogan, and P. Deslongchamps Can. J. Chem. 70 1992 1406 1426
320. R. Ruel, and P. Deslongchamps Tetrahedron Lett. 31 1990 3961 3964
321. R. Ruel, and P. Deslongchamps Can. J. Chem. 70 1992 1939 1949
322. L. Zegelman, A. Hassner, Z. Mendel, and E. Dunkelblum Tetrahedron Lett. 34 1993 5641 5644
323. J. Dyer, S. Keeling, and M.G. Moloney Tetrahedron Lett. 37 1996 4573 4576
324. S. Batra, D. De, M. Seth, and A.P. Bhaduri J. Chem. Res. (S) 1993 202 [J. Chem. Res. (M) 1993, 1228]
325. V.V. Shchepin, and D.V. Fotin Chem. Heterocycl. Compd. 38 2002 1430 1431
326. V.V. Shchepin, D.V. Fotin, and S.N. Shurov Russ. J. Org. Chem. 39 2003 1231 1233
327. R. Menicagli, and S. Samaritani Tetrahedron 52 1996 1425 1432
328. S.N. Mazumdar, and M.P. Mahajan Tetrahedron Lett. 31 1990 4215 4218
329. E. Vedejs, and S.M. Duncan J. Org. Chem. 65 2000 6073 6081
330. C.H. Heathcock, R.B. Ruggeri, and K.F. McClure J. Org. Chem. 57 1992 2585 2594
331. J. Inanaga, Y. Yokoyama, Y. Handa, and M. Yamaguchi Tetrahedron Lett. 32 1991 6371 6374
332. G.A. Molander, J.B. Etter, L.S. Harring, and P.J. Thorel J. Am. Chem. Soc. 113 1991 8036 8045
333. K. Fujita, and K. Mori Eur. J. Org. Chem. 2001 493 502
334. I. Shiina, K. Uoto, N. Mori, T. Kosugi, and T. Mukaiyama Chem. Lett. 1995 181 182
335. T. Takemura, Y. Nishii, S. Takahashi, J. Kobayashi, and T. Nakata Tetrahedron 58 2002 6359 6365
336. S. Inoue, Y. Iwabuchi, H. Irie, and S. Hatakeyama Synlett 1998 735 736
337. P.P. Reddy, K.-F. Yen, and B.-J. Uang J. Org. Chem. 67 2002 1034 1035
338. M. Inoue, M. Sasaki, and K. Tachibana J. Org. Chem. 64 1999 9416 9429
339. M. Inoue, M. Sasaki, and K. Tachibana Tetrahedron 55 1999 10949 10970
340. M. Inoue, M. Sasaki, and K. Tachibana Tetrahedron Lett. 38 1997 1611 1614
341. Ichikawa, S.; Minakawa, N.; Shuto, S.; Tanaka, M.; Sasaki, T.; Matsuda, A. Nucl. Acids Symp. Ser. 1996, 35 (33th Symposium on Nucleic Acids Chemistry, 1996), 13-14. (b) S. Ichikawa, S. Shuto, N. Minakawa, and A. Matsuda J. Org. Chem. 62 1997 1368 1375
342. Ichikawa, S.; Minakawa, N.; Shuto, S.; Tanaka, M.; Sasaki, T.; Matsuda, A. Nucl. Acids Symp. Ser. 1996, 35 (33th Symposium on Nucleic Acids Chemistry, 1996), 13-14.. (b) S. Ichikawa, S. Shuto, N. Minakawa, and A. Matsuda J. Org. Chem. 62 1997 1368 1375
343. S. Yamada, A. Tanaka, and T. Oritani Biosci. Biotech. Biochem. 59 1995 1657 1660
344. T. Nagamitsu, D. Tacano, T. Fukuda, K. Otoguro, I. Kuwajima, Y. Harigaya, and S. Omura Org. Lett. 6 2004 1865 1867
345. G.A. Molander, G.A. Brown, and I. Storch de Gracia J. Org. Chem. 67 2002 3459 3463
346. S.-J. Kim, H.-Y. Kang, and D.H. Sherman Synthesis 2001 1790 1793
347. S. Fukuzawa, M. Miura, and H. Matsuzawa Tetrahedron Lett. 42 2001 4167 4169
348. M. Nerz-Stormes, and E.R. Thornton J. Org. Chem. 56 1991 2489
349. M. Obringer, F. Colobert, B. Neugnot, and G. Solladié Org. Lett. 5 2003 629 632
350. D. Basavaiah, and T.K. Bharathi Tetrahedron Lett. 32 1991 3417 3420
351. A.S. Kende, K. Kawamura, and R.J. DeVita J. Am. Chem. Soc. 112 1990 4070 4072
352. M.A. Blaskovich, and G.A. Lajoie J. Am. Chem. Soc. 115 1993 5021 5030
353. Y. Ding, J. Wang, K.A. Abboud, Y. Xu, W.R. Dolbier Jr., and N.G.J. Richards J. Org. Chem. 66 2001 6381 6388
354. J. Brocard, M. Mahmoudi, L. Pelinski, and L. Maciejewski Tetrahedron 46 1990 6995 7002
355. (a) A. Sorochinsky, N. Voloshin, A. Markovsky, M. Belik, N. Yasuda, H. Uekusa, T. Ono, D.O. Berbasov, and V.A. Soloshonok J. Org. Chem. 68 2003 7448 7454
356. (b) V.A. Soloshonok, H. Ohkura, A. Sorochinsky, N. Voloshin, A. Markovsky, M. Belik, and T. Yamazaki Tetrahedron Lett. 43 2002 5445 5448
357. (c) Sorochinsky, A.; Berbasov, D. O.; Soloshonok, V. A. Abstr. Pap.-Am. Chem. Soc. 2003, 226th. ORGN-530.
358. D.D. Staas, K.L. Savage, C.F. Homnick, N.N. Tsou, and R.G. Ball J. Org. Chem. 67 2002 8276 8279
359. C.M.R. Ribeiro, E.S. Santos, A.H.O. Jardim, M.P. Maia, F.C. da Silva, A.P.D. Moreira, and V.F. Ferreira Tetrahedron: Asymmetry 13 2002 1703 1706
360. A. Mi, Z. Wang, J. Zhang, and Y. Jiang Synth. Commun. 27 1997 1469 1473
361. A. Mi, Z. Wang, Z. Chen, and Y. Jiang Tetrahedron: Asymmetry 6 1995 2641 2642
362. J.M. Andrés, Y. Martin, R. Pedrosa, and A. Perez-Encabo Tetrahedron 53 1997 3787 3794
363. K. Soai, and Y. Kawase Tetrahedron: Asymmetry 2 1991 781 784
364. D. Pini, G. Uccello-Barretta, A. Mastantuono, and P. Salvadori Tetrahedron 53 1997 6065 6072
365. D. Pini, A. Mastantuono, and P. Salvadori Tetrahedron: Asymmetry 5 1994 1875 1876
366. A. Mastantuono, D. Pini, C. Rolfini, and P. Salvadori Chirality 7 1995 499 504
367. K. Soai, A. Oshio, and T. Saito J. Chem. Soc., Chem. Commun. 1993 811 812
368. K. Seki, M. Tatuzawa, and S. Fukuzawa Kidorui 30 1997 282 283
369. A. Ojida, T. Yamano, N. Taya, and A. Tasaka Org. Lett. 4 2002 3051 3054
370. D.H. Park, H.J. Choi, and S.-G. Lee J. Kor. Chem. Soc. 47 2003 597 600
371. Y. Zhang, and W. Wu Tetrahedron: Asymmetry 8 1997 3575 3578
372. Z.Y. Wang, J. Shen, C.S. Jiang, and T.P. You Chin. Chem. Lett. 11 2000 659 662
373. C. Jiang, D. Li, Q. Cheng, Y. Ke, and T. You Huaxue Tongbao 2001 637 640
374. J.S. Yadav, T.K. Praveen Kumar, and P.P. Maniyan Tetrahedron Lett. 34 1993 2969 2972
375. E. Greiner, J.E. Folk, A.E. Jacobson, and K.C. Rice Bioorg. Med. Chem. 12 2004 233 238
376. H. Kigoshi, M. Kita, S. Ogawa, M. Itoh, and D. Uemura Org. Lett. 5 2003 957 960
377. A.P. VanSickle, and H. Rapoport J. Org. Chem. 55 1990 895 901
378. F. Orsini, and F. Pelizzoni Carbohydr. Res. 243 1993 183 189
379. A. Fkyerat, N. Burki, and R. Tabacchi Tetrahedron: Asymmetry 7 1996 2023 2028
380. P.K. Zubaidha, S.P. Chavan, U.S. Racherla, and N.R. Ayyangar Tetrahedron 47 1991 5759 5768
381. T.K. Karpha, M. Ghosal, and D. Mukherjee Indian J. Chem. Sect. B. 1990 301 303
382. S.H. Lee, S.-G. Lee, C.E. Song, I.O. Kim, and B.Y. Chung Kor. J. Med. Chem. 7 1997 34 40
383. T.R. Johnson, and R.B. Silverman Bioorg. Med. Chem. 7 1999 1625 1636
384. R. Kalyanakumar, M.S. Chadha, A. Chattopadhyay, and V.R. Mamdapur Indian J. Chem. Sect. B. 35B 1996 356 358
385. V. Grassberger, A. Berger, K. Dax, M. Fechter, G. Gradnig, and A.E. Stuetz Liebigs Ann. Chem. 1993 379 380
386. A.R. McKinney, and D.D. Ridley Aust. J. Chem. 54 2001 757 761
387. M. Iwashima, H. Nagaoka, K. Kobayashi, and Y. Yamada Tetrahedron Lett. 33 1992 81 82
388. M.F. Vaezi, M. Alam, B.P. Sani, T.S. Rogers, L. Simpson-Herren, J.J. Wille, D.L. Hill, T.I. Doran, W.J. Brouillette, and D.D. Muccio J. Med. Chem. 37 1994 4499 4507
389. C.Y. Cheng, S.C. Wu, L.W. Hsin, and S.W. Tam J. Med. Chem. 35 1992 2243 2247
390. Q. Lu, W.H. Duan, and J.C. Cai Chin. Chem. Lett. 13 2002 113 114
391. T. Kurosawa, M. Fujiwara, H. Nakano, M. Sato, T. Yoshimura, and T. Murai Steroids 66 2001 499 504
392. W. Yuan, B. Munoz, C.-H. Wong, J.Z. Haeggstroem, A. Wetterholm, and B. Samuelsson J. Med. Chem. 36 1993 211 220
393. D.W. McPherson, D.L. DeHaven-Hudkins, A.P. Callahan, and F.F. Knapp Jr. J. Med. Chem. 36 1993 848 854
394. M. Adamczyk, D.D. Johnson, and R.E. Reddy Bioconjugate Chem. 9 1998 403 408
395. M. Zhang, L. Zhu, and X. Ma Tetrahedron: Asymmetry 14 2003 3447 3453
396. A. Presser, I. Potschger, E. Haslinger, and A. Hufner Monatsh. Chem. 133 2002 231 239
397. A. Presser, E. Haslinger, R. Weis, and A. Huefner Monatsh. Chem. 129 1998 921 930
398. R.C. Cambie, S.C. Moratti, P.S. Rutledge, R.J. Weston, and P.D. Woodgate Aust. J. Chem. 43 1990 1151 1162
399. S.P. Chavan, P.K. Zubaidha, and N.R. Ayyangar Tetrahedron Lett. 33 1992 4605 4608
400. N.S. Vostrikov, A.V. Abutkov, L.V. Spirikhin, A.A. Fatykhov, and M.S. Miftahov Russ. Chem. Bull. 50 2001 654 658
401. K. Goto, T. Kubo, K. Yamamoto, K. Nakasuji, K. Sato, D. Shiomi, T. Takui, M. Kubota, T. Kobayashi, K. Yakusi, and J. Ouyang J. Am. Chem. Soc. 121 1999 1619 1620
402. P. Ceccherelli, M. Curini, M.C. Marcotullio, and O. Rosati J. Org. Chem. 55 1990 311 315
403. R.J. Atkins, G.F. Breen, L.P. Crawford, T.J. Grinter, M.A. Harris, J.F. Hayes, C.J. Moores, R.N. Saunders, A.C. Share, T.C. Walsgrove, and C. Wicks Org. Proc. Res. Dev. 1 1997 185 197
404. A.P. Rauter, O. Oliveira, T. Canda, E. Leroi, H. Ferreira, M.J. Ferreira, and J.A. Ascenso J. Carbohydr. Chem. 21 2002 257 273
405. A. Balakumar, S. Janardhanam, and K. Rajagopalan Indian J. Chem. Sect. B 32B 1993 313 317
406. M. Hisatome, J. Watanabe, Y. Kawajiri, K. Yamakawa, and Y. Iitaka Organometallics 9 1990 497 503
407. R. Obara, and C. Wawrzenczyk J. Cosmet. Sci. 49 1998 299 308
408. For a review on fluorinated organozinc reagents in general, see: Davis, C. R.; Burton, D. J. In Organozinc Reagents; Knochel, P., Jones, P., Eds.; University Press: Oxford, 1999, p 57-76.
409. J.E. Baldwin, G.P. Lynch, and C.J. Schofield Tetrahedron 48 1992 9085 9100
410. M.R. Angelastro, P. Bey, S. Mehdi, and N.P. Peet Bioorg. Med. Chem. Lett. 2 1992 1235 1238
411. A. Otaka, J. Watanabe, A. Yukimasa, Y. Sasaki, H. Watanabe, T. Kinoshita, S. Oishi, H. Tamamura, and N. Fujii J. Org. Chem. 69 2004 1634 1645
412. T. Tsukamoto, and T. Kitazume J. Chem. Soc., Chem. Commun. 1992 540 541
413. T. Tsukamoto, and T. Kitazume J. Chem. Soc., Perkin Trans. 1 1993 1177 1181
414. S. Marcotte, X. Pannecoucke, C. Feasson, and J.-C. Quirion J. Org. Chem. 64 1999 8461 8464
415. S. Lacroix, A. Cheguillaume, S. Gerard, and J. Marchand-brynaert Synthesis 2003 2483 2486
416. H.L. Sham, D.A. Betebenner, N.E. Wideburg, D.J. Kempf, J.J. Plattner, and D.W. Norbeck J. Fluorine Chem. 73 1995 221 224
417. H.L. Sham, and D.A. Betebenner J. Chem. Soc., Chem. Commun. 1991 1134 1135
418. Y. Wang, and S. Zhu Tetrahedron Lett. 42 2001 5741 5744
419. Y. Wang, and S. Zhu Synthesis 2002 1813 1818
420. T. Tsukamoto, and T. Kitazume Synlett 1992 977 979
421. Q.-S. Hu, and C.-M. Hu J. Fluorine Chem. 83 1997 87 88
422. Kumadaki, I. Abstr. Pap.-226th ACS Meeting 2003, FLUO-010.
423. M. Kuroboshi, and T. Ishihara Bull. Chem. Soc. Jpn 63 1990 428 437
424. M. Yoshida, D. Suzuki, and M. Iyoda Synth. Commun. 26 1996 2523 2529
425. M. Yoshida, D. Suzuki, and M. Iyoda J. Chem. Soc., Perkin Trans. 1 1997 643 648
426. P.L. Coe, M. Markou, and J.C. Tatlow J. Fluorine Chem. 84 1997 113 118
427. P.L. Coe, M. Markou, and J.C. Tatlow J. Fluorine Chem. 89 1998 183 188
428. T. Allmendinger, and R.W. Lang Tetrahedron Lett. 32 1991 339 340
429. S. Kaneko, T. Yamazaki, and T. Kitazume J. Org. Chem. 58 1993 2302 2312
430. Y. Gong, and K. Kato J. Fluorine Chem. 111 2001 77 80
431. K. Murata, S. Kaneko, and T. Kitazume Bioorg. Med. Chem. Lett. 3 1993 2685 2688
432. S. Watanabe, Y. Sakai, T. Kitazume, and T. Yamazaki J. Fluorine Chem. 68 1994 59 61
433. Y. Shen, and Y. Xiang J. Fluorine Chem. 51 1991 349 355
434. Y. Shen, S. Gao, and Y. Xiang J. Fluorine Chem. 63 1993 151 155
435. Iseki, K. In Enantiocontrolled Synthesis of Fluoro-Organic Compounds: Stereochemical Challenges and Biomedical Targets; Soloshonok, V. A., Ed.; John Wiley & Sons, Ltd., 1999, chapter 2, pages 33-62.
436. T. Tsukamoto, T. Yoshiyama, and T. Kitazume Tetrahedron: Asymmetry 2 1991 759 762
437. S. Watanabe, T. Fujita, M. Sakamoto, H. Takeda, T. Kitazume, and T. Yamazaki J. Fluorine Chem. 82 1997 1 7
438. Y. Matsumura, H. Fujii, T. Nakayama, Y. Morizawa, and A. Yasuda J. Fluorine Chem. 57 1992 203 207
439. L.P. Kotra, Y. Xiang, M.G. Newton, R.F. Schinazi, Y.-C. Cheng, and C.K. Chu J. Med. Chem. 40 1997 3635 3644
440. L.P. Kotra, M.G. Newton, and C.K. Chu Carbohydr. Res. 306 1998 69 80
441. P. Meffre, R.H. Dave, J. Leroy, and B. Badet Tetrahedron Lett. 42 2001 8625 8627
442. V. Gouge, P. Jubault, and J.-C. Quirino Tetrahedron Lett. 45 2004 773 776
443. D.A. Cogan, G. Liu, and J.A. Ellman Tetrahedron 55 1999 8883 8904
444. F.A. Davis, R.T. Reddy, and R.E. Reddy J. Org. Chem. 57 1992 6387 6389
445. M. Braun, A. Vonderhagen, and D. Waldmueller Liebigs Ann. 1995 1447 1450
446. W.R. Dolbier Jr., R. Ocampo, and R. Paredes J. Org. Chem. 60 1995 5372 5373
447. R. Ocampo, W.R. Dolbier Jr., and R. Paredes J. Fluorine Chem. 88 1998 41 50
448. R. Ocampo, W.R. Dolbier Jr., M.D. Bartberger, and R. Paredes J. Org. Chem. 62 1997 109 114
449. R. Ocampo, W.R. Dolbier Jr., and F. Zuluaga Coll. Czech. Chem. Commun. 67 2002 1325 1334
450. H. Inagaki, K. Sugita, R.N. Miyauchi, S. Miyauchi, T. Takeda, M. Itoh, H. Takahashi, and M. Takemura ARKIVOC 2003 112 117
451. J.M. Altenburger, and D. Schirlin Tetrahedron Lett. 32 1991 7255 7258
452. Y. Takeuchi, A. Kanada, S. Kawahara, and T. Koizumi J. Org. Chem. 58 1993 3483 3485
453. T. Morikawa, M. Uejima, Y. Kobayashi, and T. Taguchi J. Fluorine Chem. 65 1993 79 89
454. M.C. Pirrung, E.G. Rowley, and C.P. Holmes J. Org. Chem. 58 1993 5683 5689
455. H. Fukuda, and T. Kitazume Heterocycles 46 1997 275 285
456. F. Matsuda, T. Matsumoto, M. Ohsaki, and S. Terashima Bull. Chem. Soc. Jpn 64 1991 2983 2989
457. R.P. Robinson, and K.M. Donahue J. Org. Chem. 57 1992 7309 7314
458. R. Shen, C. Priebe, C. Patel, L. Rubo, T. Su, M. Kahn, and R. Sugasawara Tetrahedron Lett. 33 1992 3417 3420
459. A.M. Doherty, J.S. Kaltenbronn, J.P. Hudspeth, J.T. Repine, W.H. Roark, I. Sircar, F.J. Tinney, C.J. Connolly, and J.C. Hodges J. Med. Chem. 34 1991 1258 1271
460. A.M. Doherty, I. Sircar, B.E. Kornberg, J. Quin III, R.T. Winters, J.S. Kaltenbronn, M.D. Taylor, B.L. Batley, and S.R. Rapundalo J. Med. Chem. 35 1992 2 14
461. J.W. Skiles, C. Miao, R. Sorcek, S. Jacober, P.W. Mui, G. Chow, S.M. Weldon, G. Possanza, and M. Skoog J. Med. Chem. 35 1992 4795 4808
462. S. Marcotte, F. D'Hooge, S. Ramadas, C. Feasson, X. Pannecoucke, and J.-C. Quirion Tetrahedron Lett. 42 2001 5879 5882
463. K. Konno, K. Ojima, T. Hayashi, and H. Takayama Chem. Pharm. Bull. 40 1992 1120 1124
464. H.S. Gill, J.M. Londowski, R.A. Corradino, A.R. Zinsmeister, and R. Kumar J. Med. Chem. 33 1990 480 490
465. N. Saito, T. Matsunaga, T. Fujishima, M. Anzai, H. Saito, K. Takenouchi, D. Miura, S. Ishizuka, H. Takayama, and A. Kittaka Org. Biomol. Chem. 1 2003 4396 4402
466. E.A. Hallinan, T.J. Hagen, R.K. Husa, S. Tsymbalov, S.N. Rao, J.P. vanHoeck, M.F. Rafferty, A. Stapelfeld, M.A. Savage, and M. Reichman J. Med. Chem. 36 1993 3293 3299
467. H. Fukuda, and T. Kitazume J. Fluorine Chem. 74 1995 171 176