Homo- and cross-olefin metathesis coupling of vinylphosphane oxides and electron-poor alkenes: Access to P-stereogenic dienophiles

Advanced Synthesis and Catalysis

Volumn 348, Issue 7-8, 2006, Pages 931-938

  Vinokurov, Nikolai ^a   Michrowska, Anna ^b   Szmigielska, Anna ^c   Drzazga, Zbigniew ^c   Wójciuk, Grzegorz ^c   Demchuk, Oleg M ^c   Grela, Karol ^b   Pietrusiewicz, K Michał ^b,c   Butenschön, Holger ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^c MARIA CURIE SK ODOWSKA UNIVERSITY   (Poland)

Author keywords

Catalysis; Metathesis; P stereogenic; Ruthenium; Vinylphosphane oxide

Indexed keywords

EID: 33744804281     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200505463     Document Type: Article

References (110)

1. General reviews on olefin metathesis reaction and catalysts: Handbook of Metathesis, (Ed.: R. H. Grubbs), Wiley-VCH, Weinheim, 2003, vols. 1-3.
2. A. Fürstner, Angew. Chem. 2000, 112, 3140-3172;
3. Angew. Chem. Int. Ed. 2000, 39, 3012-3043.
4. D. L. Wright, Curr. Org. Chem. 1999, 3, 211-240.
5. M. Schuster, S. Blechert, Angew. Chem. 1997, 109, 2124-2144;
6. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036-2056.
7. O. R. Thiel, in: Transition Metals for Organic Synthesis, (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 2004, Vol. 1, pp. 321-334.
8. R. H. Grubbs, T. M. Trnka, in: Ruthenium in Organic Synthesis (Ed.: S.-I. Murahashi), Wiley-VCH, Weinheim, 2004, pp. 153-178.
9. A. Hafner, P. A. v. d. Schaaf, A. Mühlebach, Chimia 1996, 50, 131-134.
10. S. K. Armstrong, J. Chem. Soc. Perkin Trans, 1 1998, 371-388.
11. R. H. Grubbs, S. J. Miller, G. C. Fu, Acc. Chem. Res. 1995, 28, 446-452.
12. U. Koert, Nachr. Chem. Tech. Lab. 1995, 43, 809-814.
13. A. Kinoshita, N. Sakakibara, M. Mori, J. Am. Chem. Soc. 1997, 119, 12388-12389.
14. For a recent review on enyne metathesis, see: S. T. Diver, A. J. Giessert Chem. Rev. 2004, 104, 1317-1382.
15. C. S. Poulsen, R. Madsen, Synthesis 2003, 1-18.
16. D. Sémeril, C. Bruneau, P. H. Dixneuf, Adv. Synth. Catal. 2002, 344, 585.
17. For reviews on cross-metathesis, see: a) S. J. Connon, S. Blechert, Angew. Chem. 2003, 115, 1944-1968;
18. Angew. Chem. Int. Ed. 2003, 42, 1900-1923;
19. b) A. J. Vernall, A. D. Abell, Aldrichimica Acta 2003, 36, 93.
20. a) A. K. Chatterjee, T.-L. Choi, D. P. Sanders, R. H. Grubbs, J. Am. Chem. Soc. 2003, 125, 11360-11370;
21. b) T.-L. Choi, A. K. Chatterjee, R. H. Grubbs, Angew. Chem. 2001, 113, 1317-1319;
22. Angew. Chem. Int. Ed. 2001, 40, 1277-1279.
23. For an application of styrene CM to a commercial product, see: a) R. L. Pederson, I. M. Fellows, T. A. Ung, H. Ishihara, S. P. Hajela, Adv. Synth. Catal. 2002, 344, 728-735;
24. b) for styrene CM as alternative to Heck and other cross-coupling reactions, see: A. K. Chatterjee, F. D. Toste, T.-L. Choi, R. H. Grubbs, Adv. Synth. Catal. 2002, 344, 634-637.
25. T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29.
26. V. Dragutan, I. Dragutan, A. T. Balaban, Platinum Met. Rev. 2001, 45, 155-163.
27. Applied Homogeneous Catalysis with Organometallic Compounds, (Eds.: B. Cornils, W. A. Herrmann), VCH, Weinheim, 1996, Vols. 1+2.
28. Comprehensive Asymmetric Catalysis, (Eds.: E. N. Jacobsen, A. Pfaltz, H. Yamamoto), Springer, Berlin, 1999, Vols. 1-3, pp. 1483.
29. a) W. S. Knowles, M. J. Sabacky, J. Chem. Soc. Chem. Commun. 1968, 1445-1446;
30. b) L. Horner, H. Siegel, H. Büthe, Angew. Chem. 1968, 80, 1034-1035;
31. Angew. Chem. Int. Ed. Engl. 1968, 7, 942.
32. a) T. P. Dang, H. B. Kagan, J. Chem. Soc. Chem. Commun. 1971, 481;
33. b) H. B. Kagan, T-P. Dang, J. Am. Chem. Soc. 1972, 94, 6429-6433.
34. M. D. Fryzuk, B. Bosnich, J. Am. Chem. Soc. 1978, 100, 5491-5494.
35. H. Brunner, W. Pieronczyk, Angew. Chem. 1979, 91, 655-656;
36. Angew. Chem. Int. Ed. Engl. 1979, 18, 620-621.
37. H. Takaya, K. Mashima, K. Koyano, M. Yagi, H. Kumobayashi, T. Taketomi, S. Akutagawa, R. Noyori, J. Org. Chem. 1986, 51, 629-635.
38. For reviews, see: a) W. Tang, X. Zhang Chem. Rev. 2003, 103, 3029-3069;
39. b) I. Ojima, (Ed.), Catalytic Asymmetric Synthesis, VCH, New York, 1993.
40. a) W. S. Knowles, M. J. Sabacky, B. D. Vineyard, D. J. Weinkauff, J. Am. Chem. Soc. 1975, 97, 2567-3568;
41. b) W. S. Knowles, Acc. Chem. Res. 1983, 16, 106-112.
42. a) L. Horner, H. Winkler, A. Rapp, A. Mentrup, H. Hoffmann, P. Beck, Tetrahedron Lett. 1961, 161-166;
43. b) R. D. Baechler, K. Mislow, J. Am. Chem. Soc. 1970, 92, 3090-3093.
44. a) D. Liu, W. Gao, C. Wang, X. Zhang, Angew. Chem. 2005, 777, 1715-1717;
45. Angew. Chem. Int. Ed. 2005, 44, 1687-1689;
46. b) D. Liu, X. Zhang, Eur. J. Org. Chem. 2005, 646-649;
47. c) W. Tang, D. Liu, X. Zhang, Org. Lett. 2003, 5, 205-207;
48. d) W. Tang, X. Zhang, Angew. Chem. 2002, 114, 1682-1684;
49. Angew. Chem. Int. Ed. 2002, 41, 1612-1614.
50. K. V. L. Crepy, T. Imamoto, Adv. Synth. Catal. 2003, 345, 79-101.
51. a) K. V. L. Crepy, T. Imamoto, Top. Curr. Chem. 2003, 229, 1-40;
52. b) I. D. Gridnev, T. Imamoto, Acc. Chem. Res. 2004, 37, 633-644.
53. C. R. Johnson, T. Imamoto, J. Org. Chem. 1987, 52, 2170-2174.
54. A. M. Maj, K. M. Pietrusiewicz, I. Suisse, F. Agbossou, A. Mortreux, Tetrahedron: Asymmetry 1999, 10, 831-835.
55. A. M. Maj, K. M. Pietrusiewicz, I. Suisse, F. Agbossou, A. Mortreux, J. Organomet. Chem. 2001, 626, 157-160.
56. K. M. Pietrusiewicz, M. Zablocka, J. Monkiewicz, J. Org. Chem. 1984, 49, 1522-1526.
57. K. M. Pietrusiewicz, M. Zablocka, Phosphorus and Sulfur 1988, 40, 47-51.
58. K. M. Pietrusiewicz, W. Wisniewski, W. Wieczorek, A. Brandi, Phosphorus, Sulfur and Silicon 1995, 101, 253-259.
59. A. Brandi, P. Cannavo, K. M. Pietrusiewicz, M. Zablocka, M. Wieczorek, J. Org. Chem. 1989, 54, 3073-3077.
60. a) A. Brandi, S. Chicchi, A. Goti, K. M. Pietrusiewicz, M. Zablocka, W. Wisniewski, J. Org. Chem. 1991, 56, 4383-4388;
61. b) K. M. Pietrusiewicz, Tetrahedron 1990, 46, 7093-7104.
62. C. Cardellicchio, V. Fiandanese, F. Naso, S. Pacifico, M. Koprowski, K. M. Pietrusiewicz, Tetrahedron Lett. 1994, 35, 6343-6346.
63. K. M. Pietrusiewicz, M. Zablocka, Chem. Rev. 1994, 94, 1375-1411.
64. K. M. Pietrusiewicz, W. Wisniewski, M. Zablocka, Tetrahedron 1989, 45, 337-348.
65. K. M. Pietrusiewicz, M. Zablocka, W. Wieczorek Phosphorus, Sulfur, and Silicon 1989, 42, 183-190.
66. a) T. Miura, T. Imamoto, Tetrahedron Lett. 1999, 40, 4833-4836;
67. b) T. Imamoto, S.-i. Kikuchi, T. Miura, Y. Wada, Org. Lett. 2001, 3, 87-90.
68. A. K. Chatterjee, T.-L. Choi, R. H. Grubbs, Synlett 2001, 1034-1037.
69. M. Trevitt, V. Gouverneur, Tetrahedron Lett. 1999, 40, 7333-7336.
70. M. Schuman, M. Trevitt, A. Redd, V. Gouverneur, Angew. Chem. 2000, 112, 2604-2607;
71. Angew. Chem. Int. Ed. 2000, 39, 2491-2493.
72. [16]
73. a) Diphenyl(vinyl)phosphane oxide 6c efficiently undergoes cross metathesis with various unsubstituted olefins, however, it shows no reactivity in homometathesis and in cross metathesis with methyl vinyl ketone, see: F. Bisaro, V. Gouverneur, Tetrahedron Lett. 2003, 44, 7133-7135;
74. b) For CM of di- and tri(vinyl)phosphane oxides, see: F. Bisaro, V. Gouverneur, Tetrahedron 2005, 67, 2395-2400.
75. O. M. Demchuk, K. M. Pietrusiewicz, A. Michrowska, K. Grela, Org. Lett. 2003, 5, 3217-3220.
76. a) T.-L. Choi, C. W. Lee, A. K. Chatterjee, R. H. Grubbs, J. Am. Ghem. Soc. 2001, 123, 10417-10418;
77. b) Q. Yao, A. R. Motta, Tetrahedron Lett. 2004, 45, 2447-2451;
78. c) For a very recent example of acrylonitrile homodimerization and CM with α,β-unsaturated carbonyl compounds, see: C.-X. Bai, W.-Z. Zhang, R. He, X.-B. Lua, Z.-Q. Zhang, Tetrahedron Lett. 2005, 46, 7225-7228.
79. A. K. Chatterjee, F. D. Toste, T.-L. Choi, R. H. Grubbs, Adv. Synth. Catal. 2002, 344, 634-637.
80. [18,19]
81. For a review on precatalyst II and its variations, see: A. H. Hoveyda, D. G. Gillingham, J. J. Van Veldhuizen, O. Kataoka, S. B. Garber, J. S. Kingsbury, J. P. A. Harrity, Org. Biomol. Chem. 2004, 2, 1-16.
82. Precatalyst III, see: a) K. Grela, S. Harutyunyan, A. Michrowska, Angew. Chem. Int. Ed. 2002, 41, 4038-4040;
83. Angew. Chem. 2002, 114, 4210-4212;
84. b) A. Michrowska, R. Bujok, S. Harutyunyan, V. Sashuk, G. Dolgonos, K. Grela, J. Am. Chem. Soc. 2004, 126, 9318-9325;
85. c) S. Harutyunyan, A. Michrowska, K. Grela, in: Catalysts for Fine Chemical Synthesis, (Eds.: S. M. Roberts, J. Whittall, P. Mather, P. McCormack), Wiley-Interscience, New York, 2004, Vol. 3, Chap. 9.1, pp. 169-173.
86. Precatalyst FV, see: a) M. Zaja, S. J. Connon, A. M. Dunne, M. Rivard, N. Buschmann, J. Jiricek, S. Blechert, Tetrahedron 2003, 59, 6545-6558;
87. b) N. Buschmann, H. Wakamatsu, S. Blechert, Synlett 2004, 667-670.
88. Precatalyst V, see: a) H. Wakamatsu, S. Blechert, Angew. Chem. Int. Ed. 2002, 41, 2403-2405;
89. Angew. Chem., 2002, 114, 4207-4209;
90. b) A. M. Dunne, S. Mix, S. Blechert, Tetrahedron Lett. 2003, 44, 2733-2736.
91. Precatalyst VI, see: J. A. Love, J. P. Morgan, T. M. Trnka, R. H. Grubbs, Angew. Chem. Int. Ed. 2002, 41, 4035-4037;
92. Angew. Chem. 2002, 114, 2509-2511.
93. a) Boehringer Ingelheim International GmbH, US Patent 6,867,303, 2005;
94. b) for a recent application of III in synthesis of hepatitis C antiviral agent, BILN 2061, see: Boehringer Ingelheim International GmbH, World Patent WO 2004/089974 A1, 2004;
95. b) T. Nicola, M. Brenner, K. Donsbach, P. Kreye, Org. Proc. Res. Develop. 2005, 9, 513-515.
96. For applications of III in target-oriented synthesis, see: a) (-)-securinine: T. Honda, H. Namiki, K. Kaneda, H. Mizutani, Org. Lett. 2004, 6, 87-89;
97. b) (+)-viroallosecurinine: T. Honda, H. Namiki, M. Watanabe, H. Mizutani, Tetrahedron Lett. 2004, 45, 5211-5213;
98. c) an artificial photosynthesis model: S. Ostrowski, A. Mikus, Mol. Diversity 2003, 6, 315-321.
99. [51] and the following: a) Z. Pakulski, O. M. Demchuk, R. Kwiatosz, P. W. Osiński, W. Swierczyńska, K. M. Pietrusiewicz, Tetrahedron: Asymmetry 2003, 14, 1459-1462;
100. b) M. Deshmukh, E. Dunach, S. Juge, H. B. Kagan, Tetrahedron Lett. 1984, 25, 3467-3470.
101. [52]
102. [55]
103. For an example, see: R. Bodalski, J. Koszuk, H. Krawczyk, K. M. Pietrusiewicz, J. Org. Chem. 1982, 47, 2219-2220.
104. K. M. Pietrusiewicz, W. Wisniewski, M. Zablocka, Tetrahedron 1989, 45, 337-348.
105. Y. Xu, J. Xia, H. Guo, Synthesis 1986, 691-692.
106. American Cyanamid Co., US Patent 19600927, 1962.
107. M. Maffei, G. Buono, New J. Chem. 1988, 12, 923-930.
108. K. M. Pietrusiewicz, Phosphorus, Sulfur, and Silicon 1996, 109-110, 573-576.
109. G. Salamończyk, W. Holody, A. Szmigielska, Z. Drzazga, W. Wieczorek, K. M. Pietrusiewicz, to be published.
110. See the Supporting Information for the characterization data for compounds 7a, 7b, 7e-7g, 8aIII-8aV, 8hIII, 8iIII, 11a, 11b, 11e, 12c, 12j and 14.