The asymmetric Heck reaction

Tetrahedron

Volumn 53, Issue 22, 1997, Pages 7371-7395

  Shibasaki, Masakatsu ^a   Boden, Christopher D J ^a,b   Kojima, Akihiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b Nippon Glaxo Ltd   (Japan)

Author keywords

Arylation; Asymmetric Heck; Carbopalladation; Quaternary; Vinylation

Indexed keywords

2 AMINOBICYCLO[2.2.1]HEPTANE 2 CARBOXYLIC ACID; DECALIN DERIVATIVE; EPTAZOCINE; FURAN DERIVATIVE; INDAN DERIVATIVE; INDOLIZIDINE DERIVATIVE; OXEPINE DERIVATIVE; PYRROLE DERIVATIVE; SESQUITERPENE; SILANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030995738     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00437-7     Document Type: Review

References (90)

1. Heck, R. F. J. Am. Chem. Soc., 1968, 90, 5518.
2. For the first example using aryl and vinyl halides, see Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn., 1971, 44, 581.
3. Heck, R. F.; Nolley Jr., J. P. J. Org. Chem., 1972, 37, 2320.
4. For a comprehensive survey of synthetic organopalladium chemistry, see Tsuji, J. Palladium Reagents and Catalysts; John Wiley & Sons: New York, 1995.
5. For a review of recent developments, see de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl., 1994, 33, 2379.
6. For an earlier review concentrating on intramolecular AHR to give tertiary centres, see Shibasaki, M.; Sodeoka, M. J. Syn. Org. Chem. Jpn., 1994, 52, 956.
7. The contribution of the Overman group to AHR development is briefly reviewed in Overman, L. E. Pure Appl. Chem., 1994, 66, 1423.
8. See Kagan, H. B.; Diter, P.; Gref, A.; Guillaneux, D.; Masson-Szymczak, A.; Rebi ère, F.; Riant, O.; Samuel, O.; Taudien, S. Pure Appl. Chem., 1996, 68, 29 and references quoted therein.
9. Heck's 1985 book gives an overview of the non-asymmetric reaction; Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: London, 1985.
10. Heck, R. F. Acc. Chem. Res., 1979, 12, 146.
11. For a review of the intramolecular Heck, see Gibson, S. E.; Middleton, R. J. Contemp. Org. Synth., 1996, 3, 447.
12. Cabri, W.; Candiani, I. Acc. Chem. Res., 1995, 28, 2.
13. However, for recent general mechanistic work of interest, see Brown, J. M.; Perez-Torrente, J. J.; Alcock, N. W.; Clase, H. J. Organometallics, 1995, 14, 207.
14. Brown, J. M.; Hii, K. K. Angew. Chem., Int. Ed. Engl., 1996, 35, 657.
15. Grigg, R.; Loganathan, V.; Santhamukar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett., 1991, 32, 687.
16. Abelman, M. M.; Oh, T.; Overman, L. E. J. Org. Chem., 1987, 52, 4130.
17. Karabelas, K.; Westerlund, C.; Hallberg, A. J. Org. Chem., 1985, 50, 3896.
18. Ozawa, F.; Kubo, A.; Hayashi, T. J. Am. Chem. Soc., 1991, 113, 1417.
19. Cabri, W.; Candiani, I.; DeBernardinis, S.; Francalanci, F.; Penco, S.; Santi, R. J. Org. Chem., 1991, 56, 5796.
20. Sato, Y.; Sodeoka, M.; Shibasaki, M. Chem. Lett., 1990, 1953.
21. Dekker, G. P. C. M.; Elsevier, C. J.; Vrieze, K.; van Leeuwen, P. W. N. M. Organometallics, 1992, 11, 1598.
22. Cabri, W.; Candiani, I.; Bedeschi, A.; Penco, S.; Santi, R. J. Org. Chem., 1992, 57, 1481.
23. Sato, Y.; Sodeoka, M.; Shibasaki, M. J. Org. Chem., 1989, 54, 4738.
24. Hayashi, T.; Matsumoto, Y.; Ito, Y. J. Am. Chem. Soc., 1988, 110, 5579.
25. Sato, Y.; Watanabe, S.; Shibasaki, M. Tetrahedron Lett., 1992, 35, 2589.
26. Danishefsky, S.; Schuda, P. F.; Kitahara, T.; Etheridge, S. J. J. Am. Chem. Soc., 1977, 99, 6066.
27. Kondo, K.; Sodeoka, M.; Mori, M.; Shibasaki, M. Tetrahedron Lett., 1993, 34, 4219.
28. Kondo, K.; Sodeoka, M.; Mori, M.; Shibasaki, M. Synthesis, 1993, 920.
29. Ohrai, K.; Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc., 1994, 116, 11737.
30. Sato, Y.; Honda, T.; Shibasaki, M. Tetrahedron Lett., 1992, 33, 2593.
31. Sato, Y.; Mori, M.; Shibasaki, M. Tetrahedron: Asymmetry, 1995, 6, 757.
32. Fukuzawa, A.; Sato, H.; Masamune, T. Tetrahedron Lett., 1987, 28, 4303.
33. Hayashi, T.; Mise, T.; Kumada, M. Tetrahedron Lett., 1976, 17, 4351.
34. Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett., 1993, 34, 4965.
35. Sato, Y.; Nukui, S.; Sodeoka, M.; Shibasaki, M. Tetrahedron, 1994, 50, 371.
36. Nukui, S.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Org. Chem., 1995, 60, 398.
37. Nylund, C. S.; Klopp, J. M.; Weinreb, S. M. Tetrahedron Lett., 1994, 35, 4287.
38. Kagechika, K.; Shibasaki, M. J. Org. Chem., 1991, 56, 4093.
39. Kagechika, K.; Ohshima, T.; Shibasaki, M. Tetrahedron, 1993, 49, 1773.
40. Shibasaki, M.; Mase, T.; Ikegami, S. J. Am. Chem. Soc., 1986, 108, 2090.
41. Ohshima, T.; Kagechika, K.; Adachi, M.; Sodeoka, M.; Shibasaki, M. J. Am. Chem. Soc., 1996, 118, 7108.
42. (a) Tietze, L. F.; Schimpf, R. Angew. Chem., Int. Ed. Engl., 1994, 33, 1089.
43. (b) Tietze, L. F.; Burkhardt, O. Liebigs Ann. Chem., 1995, 1153.
44. Tietze, L. F.; Raschke, T. Synlett, 1995, 597.
45. Tietze, L. F.; Raschke, T. Liebigs Ann. Chem., 1996, 1981.
46. Hayashi, T.; Kubo, A.; Ozawa, F. Pure Appl. Chem., 1992, 64, 421.
47. Ozawa, F.; Kubo, A.; Matsumoto, Y.; Hayashi, T.; Nishioka, E.; Yanagi, K.; Moriguchi, K. Organometallics, 1993, 12, 4188.
48. Ozawa, F.; Kobatake, Y.; Hayashi, T. Tetrahedron Lett., 1993, 34, 2505.
49. Hillers, S.; Reiser, O. Tetrahedron Lett., 1993, 34, 5265.
50. Kurihara, Y.; Sodeoka, M.; Shibasaki, M. Chem. Pharm. Bull., 1994, 42, 2357.
51. Sakamoto, T.; Kondo, Y.; Yamanaka, H. Tetrahedron Lett., 1992, 33, 6845.
52. Gao, Y.; Sharpless, K. B. J. Org. Chem., 1988, 53, 4081.
53. Ozawa, F.; Hayashi, T. J. Organomet. Chem., 1992, 428, 267.
54. Sonesson, C.; Larhed, M.; Nyqvist, C.; Hallberg, A. J. Org. Chem., 1996, 61, 4756.
55. Ripa, L.; Hallberg, A. J. Org. Chem., 1996, 61, 7147.
56. Koga, Y.; Sodeoka, M.; Shibasaki, M. Tetrahedron Lett., 1994, 35, 1227.
57. Takano, S.; Samizu, K.; Ogasawara, K. Synlett, 1993, 393.
58. Loiseleur, O.; Meier, P.; Pfaltz, A. Angew. Chem., Int. Ed. Engl., 1996, 35, 200.
59. Brunner, H.; Kramler, K. Synthesis, 1991, 1121.
60. Sakuraba, S.; Awano, K.; Achiwa, K. Synlett, 1994, 291.
61. Sakuraba, S.; Okada, T.; Morimoto, T.; Achiwa, K. Chem. Pharm. Bull., 1995, 43, 927.
62. Ozawa, F.; Kobatake, Y.; Kubo, A.; Hayashi, T. J. Chem. Soc., Chem. Commun., 1994, 1323.
63. Moinet, C.; Fiaud, J.-C. Tetrahedron Lett., 1995, 36, 2051.
64. For a recent review, see Fuji, K. Chem. Rev., 1993, 93, 2037.
65. Carpenter, N. E.; Kucera, D. J.; Overman, L. E. J. Org. Chem., 1989, 54, 5846.
66. Ashimori, A.; Overman, L. E. J. Org. Chem., 1992, 57, 4571.
67. Ashimori, A.; Matsuura, T.; Overman, L. E.; Poon, D. J. J. Org. Chem., 1993, 58, 6949.
68. Yu, Q.-S.; Brossi, A. Heterocycles, 1988, 27, 745.
69. Takemoto, T.; Sodeoka, M.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc., 1993, 115, 8477.
70. Kojima, A.; Takemoto, T.; Sodeoka, M.; Shibasaki, M. J. Org. Chem., 1996, 61, 4876.
71. For an alternative synthesis of this aldehyde, with implicit X-ray verification of its absolute configuration, see Hulme, A. N.; Henry, S. S.; Meyers, A. I. J. Org. Chem., 1995, 60, 1265.
72. Tietze, L. F. Chem. Rev., 1996, 96, 115.
73. Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl., 1993, 32, 131.
74. Kondo, K.; Sodeoka, M.; Shibasaki, M. J. Org. Chem., 1995, 60, 4322.
75. Kondo, K.; Sodeoka, M.; Shibasaki, M. Tetrahedron: Asymmetry, 1995, 6, 2453.
76. Pfaltz, A. Acta Chem. Scand., 1996, 50, 189.
77. One must be careful in making this comparison, however, as the major products obtained using the different ligand systems are isomeric.
78. Killers, S.; Sartori, S.; Reiser, R. J. Am. Chem. Soc., 1996, 118, 2087.
79. For a recent review, see Balkenhohl, F.; von dem Bussche-Hünnefeld, C.; Lansky, A.; Zechel, C. Angew. Chem., Int. Ed. Engl., 1996, 35, 2288.
80. Thompson, L. A.; Ellman, J. A. Chem. Rev., 1996, 96, 555.
81. Yun, W.; Mohan, R. Tetrahedron Lett., 1996, 37, 7189.
82. Gilbertson, S. R.; Wang, X. Tetrahedron Lett., 1996, 37, 6475.
83. Wipf, P.; Miller, C. P. Tetrahedron Lett., 1992, 33, 6267.
84. Wipf, P.; Miller, C. P. J. Org. Chem., 1993, 58, 1575.
85. For several examples of this in total syntheses, see Wipf, P. Chem. Rev., 1995, 95, 2115.
86. Maddaford, S. P.; Andersen, N. G.; Cristofoli, W. A.; Keay, B. A. J. Am. Chem. Soc., 1996, 118, 10766.
87. For a comprehensive review of Pd-mediated cascade carbopalladation reactions, see Negishi, E.; Copéret, C.; Ma, S.; Liou, S.; Liu, F. Chem. Rev., 1996, 96, 365. A number of other articles in this issue touch on the subject of sequential metal-mediated transformations.
88. Trost, B. M. Angew. Chem., Int. Ed. Engl., 1995, 34, 259.
89. Addendum. After submitting this review article, two important papers have appeared. For a paper entitled "Asymmetric Heck Reactions via Neutral Intermediates: Enhaced Enantioselectivity with Halide Additives Gives Mechanistic Insights," see Overman, L. E.; Poon, D. J. Angew. Chem. Int. Ed. Engl. 1997, 36, 518, and for a paper entitled "Synthesis and Evaluation of a New Chiral Arsine Ligand; 2,2′-bis(diphenylarsino)-1,1′-binaphthyl (BINAs)," see Kojima, A.; Boden, C. D.J.; Shibasaki, M. Tetrahedron Lett., in press (Scheme 28). (equation presented)
90. Addendum. After submitting this review article, two important papers have appeared. For a paper entitled "Asymmetric Heck Reactions via Neutral Intermediates: Enhaced Enantioselectivity with Halide Additives Gives Mechanistic Insights," see Overman, L. E.; Poon, D. J. Angew. Chem. Int. Ed. Engl. 1997, 36, 518, and for a paper entitled "Synthesis and Evaluation of a New Chiral Arsine Ligand; 2,2′-bis(diphenylarsino)-1,1′-binaphthyl (BINAs)," see Kojima, A.; Boden, C. D.J.; Shibasaki, M. Tetrahedron Lett., in press (Scheme 28). (equation presented)