Chiral allylic and allenic metal reagents for organic synthesis

Journal of Organic Chemistry

Volumn 72, Issue 22, 2007, Pages 8153-8166

  Marshall, James A ^a  

^a UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDIUM; SILICON; SYNTHESIS (CHEMICAL); TIN; ZINC;

ALLENIC METAL REAGENTS; CHIRAL ALLYLIC; ORGANIC SYNTHESIS; ORGANOMETAL COMPOUNDS;

ORGANOMETALLICS;

ALLENE DERIVATIVE; ALLYL COMPOUND; INDIUM; NATURAL PRODUCT; ORGANOMETALLIC COMPOUND; REAGENT; SILICON; TIN; ZINC;

ADDITION REACTION; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; ISOMERIZATION; REACTION ANALYSIS; REVIEW; SYNTHESIS;

BIOLOGICAL FACTORS; INDIUM; MACROCYCLIC COMPOUNDS; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; SILICON; STEREOISOMERISM; TIN; ZINC;

EID: 35548994614     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070787c     Document Type: Review

References (96)

1. (a) Dauben, W. G.; Thiesen, W. E.; Resnich, P. R. J. Am. Chem. Soc. 1962, 84, 2015.
2. (b) Kobayashi, H.; Akiyoshi, S. Bull. Chem. Soc. Jpn. 1962, 35, 1044.
3. Weinheimer, A. J.; Chang, C. W.; Matson, J. A. Prog. Chem. Nat. Prod. 1979, 36, 281.
4. (a) Saito, Y; Takayawa, H.; Konishi, S.; Yoshida, D.; Mizusaki, S. Carcinogenesis 1985, 6, 1189.
5. (b) Roberts, D. L.; Rowland, R. L. Bull. Chem. Soc. Jpn. 1962, 35, 1044.
6. (c) Springer, J. P.; Clardy, I.; Cox, RT. H.; Cutler, H. G.; Cole, P. J. Tetrahedron Lett. 1975, 2737.
7. (a) Marshall, J. A.; Robinson, E. D.; Adams, R. D. Tetrahedron Lett. 1988, 29, 4913.
8. (b) Marshall, J. A.; Robinson, E. D.; Leberton, J. J. Org. Chem. 1990, 55, 227.
9. Marshall, J. A.; Cleary, D. G. J. Org. Chem. 1986, 51, 858.
10. An elegant synthesis of the natural product was reported in 1983. Still, W. C.; Mobilio, D. J. Org. Chem. 1983, 48, 4786.
11. Marshall, J. A.; DeHoff, B. S. Tetrahedron 1987, 43, 4849.
12. Coll, J. C.; Mitchell, S. J.; Stokie, G. Aust. J. Chem. 1977, 30, 1859.
13. (a) Denmark, S. E.; Weber, E. J. J. Am. Chem. Soc. 1984, 106, 7970.
14. (b) Denmark, S. E.; Weber, E. J.; Wilson, T. M.; Wilson, T. M Tetrahedron 1989, 45, 1053.
15. Keck, G. E.; Boden, D. E. Tetrahedron Lett. 1984, 25, 1879.
16. Yamamoto, Y.; Yatagi, H.; Ishihari, Y.; Maeda, N.; Maruyama, K. Tetrahedron 1984, 40, 2239.
17. (a) Jephcote, V. J.; Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1984, 800.
18. (b) Pratt, A. J.; Thomas, E. J. J. Chem. Soc., Chem. Commun. 1982, 1115.
19. Keck, G. E.; Abbott, D. E.; Boden, E. P.; Enholm, E. J. Tetrahedron Lett. 1984, 25, 3927.
20. Marshall, J. A.; DeHoff, B. S. J. Org. Chem. 1986, 51, 858.
21. (a) Marshall, J. A.; DeHoff, B. S.; Crooks, S. L. Tetrahedron Lett. 1987, 28, 527.
22. (b) Marshall, J. A.; Crooks, S. L. Tetrahedron Lett. 1987, 28, 5081.
23. Marshall, J. A.; Crooks, S. L.; DeHoff, B. S. J. Org. Chem. 1988, 53, 1616.
24. Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1988, 29, 1657.
25. Narasaka, K.; Moriwaka, A.; Saigo, K.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1977, 50, 2773.
26. Marshall, J. A.; Gung, W. Y. Tetrahedron 1989, 45, 1045.
27. Noyori, R.; Tomino, I.; Tanimoto, Y.; Nishizawa, M. J. Am. Chem. Soc. 1984, 106, 6709.
28. Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1988, 29, 3899.
29. Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1989, 30, 309.
30. Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1989, 30, 2183.
31. Marshall, J. A.; Gill, K. J. Organomet. Chem. 2001, 624, 294.
32. (a) Marshall, J. A.; Welmaker, G. S. Tetrahedron Lett. 1991, 32, 2101.
33. (b) Marshall, J. A.; Welmaker, G. S. J. Org. Chem. 1992, 57, 7158.
34. Lipshutz, B. H.; Ellsworth, E. L.; Dimock, S. H.; Reuter, D. C. Tetrahedron Lett. 1987, 28, 143.
35. Marshall, J. A.; Jablonowski, J. A.; Elliott, L. M. J. Org. Chem. 1995, 60, 2662.
36. Marshall, J. A.; Luke, G. P. J. Org. Chem. 1991, 56, 483.
37. Marshall, J. A.; Beaudoin, S. J. Org. Chem. 1996, 61, 581.
38. Marshall, J. A.; Beaudoin, S.; Lewinski, K. J. Org. Chem. 1993, 58, 5876.
39. Saito, S.; Moriwaka, Y.; Moriwake, T. J. Org. Chem. 1990, 55, 5424.
40. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
41. Marshall, J. A.; Seletsky, B.; Luke, G. P. J. Org. Chem. 1994, 59, 3413.
42. Aldol reviews: (a) Heathcock, C. H. The Aldol Reaction: Acid and General Base Catalysis. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 133-180.
43. (b) Heathcock, C. H. The Aldol Reaction: Group I and Group II Enolates. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 181-238.
44. (c) Moon Kim, B.; Williams, S. F.; Masamune, S. The Aldol Reaction: Group III Enolates. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991 ; Vol. 2, pp 239-276.
45. (d) Paterson, I. The Aldol Reaction: Transition Metal Enolates. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, pp 301-320.
46. Ruitenberg, K.; Westmijze, H.; Meijer, J.; Elsevier, C. J.; Vermeer, P. J. Organomet. Chem. 1983, 241, 417.
47. Lequan, M.; Guillerm, G. J. Organomet. Chem. 1973, 54, 153.
48. Mukaiyama, T.; Harada, T. Chem. Lett. 1981, 621.
49. (a) Nokami, J.; Tamaoka, T.; Koguchi, T.; Okawara, R. Chem. Lett. 1984, 1939.
50. (b) Boaretto, A.; Marton, D.; Tagliavivi, G. J. Organomet. Chem. 1985, 286, 9.
51. Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1990, 55, 6246.
52. Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 3387.
53. Look, S. A.; Burch, M. T.; Fenical, W.; Qui-tai, Z.; Clardy, J. J. Org. Chem. 1985, 50, 5741.
54. Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1991, 56, 3211.
55. Marshall, J. A.; Wang, X.-j. J. Org. Chem. 1992, 57, 1242.
56. Marshall, J. A.; Perkins, J. J. Org. Chem. 1994, 59, 3509.
57. Marshall, J. A.; Yu, Y. H.; Perkins, J. F. J. Org. Chem. 1995, 60, 5550.
58. Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1997, 62, 6001.
59. Marshall, J. A.; Adams, N. D. J. Org. Chem. 1997, 62, 8976.
60. Kobayashi, S.; Nishio, K. J. Am. Chem. Soc. 1995, 117, 6392.
61. For a recent summary of their systematic studies of Lewis base promoted reactions of chlorosilanes, see: Denmark, S. E; Fu, J.; Lawler, M. J. J. Org. Chem. 2006, 71, 1523.
62. Marshall, J. A.; Wolf, M. A.; Wallace, E. M. J. Org. Chem. 1997, 62, 367.
63. Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1997, 62, 4313.
64. Tamaru, Y.; Tanaka, A.; Yasui, K.; Goto, S.; Tanaka, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 787.
65. (a) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1998, 63, 3812.
66. (b) Marshall, J. A.; Adams, N. D. J. Org. Chem. 1999, 64, 5201.
67. Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 696.
68. Burgess, K.; Jennings, L. D. J. Am. Chem. Soc. 1991, 113, 6129.
69. Panek, J. S.; Clark, T. D. J. Org. Chem. 1992, 57, 4323.
70. Marshall, J. A.; Chobanian, H. R. J. Org. Chem. 2000, 65, 8357.
71. Marshall, J. A.; Yanik, M. M.; Adams, N. D.; Ellis, K. C.; Chobanian, H. R. Org. Synth. 2004, 81, 157.
72. Matsumura, K.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 8738.
73. Marshall, J. A.; Eidam, P.; Eidam, H. S. J. Org. Chem. 2006, 71, 4840.
74. Fujii, A.; Hashiguchi, S.; Uematsu, N.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1996, 118, 2521.
75. Fleming, I.; Terrett, N. K. J. Organomet. Chem. 1984, 264, 99.
76. Marshall, J. A.; Maxson, K. J. Org. Chem. 2000, 65, 630.
77. Danheiser, R. L.; Carini, D. J.; Kwasigoch, C. A. J. Org. Chem. 1986, 51, 3870.
78. Zincophorin: (a) Marshall, J. A.; Palovich, M. R. J. Org. Chem. 1998, 63, 3701.
79. Discodermolide: (b) Marshall, J. A.; Johns, B. A. J. Org. Chem. 1998, 63, 7885.
80. Callystatin A: (c) Marshall, J. A.; Fitzgerald, R. A. J. Org. Chem. 1999, 64, 4477.
81. Aplyronine A: (d) Marshall, J. A.; Johns, B. A. J. Org. Chem. 2000, 65, 1501.
82. Bafilomycin: (e) Marshall, J. A.; Adams, N. D. Org. Lett. 2000, 2, 2897.
83. Tautomycin: (f) Marshall, J. A.; Yanik, M. J. Org. Chem. 2001, 66, 1373.
84. (-)-Callystatin A: (g) Marshall, J. A.; Bourbeau, M. P. J. Org. Chem. 2002, 67, 2751;
85. Org. Lett. 2002, 4, 3931.
86. Membrenone C: (h) Marshall, J. A.; Ellis, K. C. Org. Lett. 2003, 5, 1729.
87. Leptofuranin D: (i) Marshall, J. A.; Schaaf, G. M. J. Org. Chem. 2003, 68, 7428.
88. Vancosamine: (j) Parker, K. A.; Chang, W. Org. Lett. 2003, 5, 3891.
89. Zincophorin: (k) Defosseux, M.; Blanchard, N.; Meyer, C.; Cossy, J. Org. Lett. 2003, 5, 4037.
90. Cytostatin: (l) Marshall, J. A.; Ellis, K. Tetrahedron Lett. 2004, 45, 1351.
91. 1-Deoxy-D-galactohomonojirimycin: (m) Achmatowicz, M.; Hegedus, L. S. J. Org. Chem. 2004, 69, 2229.
92. Amphidinolide X: (n) Lepage, O.; Kattnig, E.; Fürstner, A. J. Am. Chem. Soc. 2004, 126, 15970.
93. Crocacin A-D: (o) Besev, M.; Brehm, C.; Fürstner, A. Collect. Czech. Chem. Commun. 2005, 70, 1696.
94. Dictyostatin (C10-C23): (p) Prusov, E.; Röhm, H.; Maier, M. E. Org. Lett. 2006, 8, 1025.
95. epi-Amphidinolide X: (q) Fürstner, A.; Kattnig, E.; Lepage, O. J. Am. Chem. Soc. 2006, 128, 9194.
96. Branimycin (C13-C18): (r) Felzmann, W.; Castagnolo, D.; Rosenbeiger, D.; Mulzer, J. J. Org. Chem. 2007, 72, 2182.