Nucleophilic cyclopropanation reaction with bis(iodozincio)methane by 1,4-addition to α,β-unsaturated carbonyl compounds

Chemistry - An Asian Journal

Volumn 4, Issue 8, 2009, Pages 1298-1303

  Nomura, Kenichi ^a   Hirayama, Takaharu ^a   Matsubara, Seijiro ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

Cyclopropanation; Dia stereoselectivity; Enols; Nucleo philic addition; Silylation

Indexed keywords

CYCLOPROPANATION; DIA-STEREOSELECTIVITY; ENOLS; NUCLEO-PHILIC ADDITION; SILYLATION;

CARBONYLATION; CYANIDES; ETHERS; KETONES; METHANE; SILANES; STEREOSELECTIVITY; UNSATURATED COMPOUNDS;

ADDITION REACTIONS;

EID: 68349141864     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900123     Document Type: Article

References (91)

1. A few selected recent examples: a) S. Ay, M. Nieger, S. Bräse, Chem. Eur. J. 2008, 14, 11539;
2. b) V. Komanduri, F. Pedraza, M.J. Krische, Adv. Synth. Catal. 2008, 350,1569;
3. c) X. Rathgeb, S. March, A. Alexakis, J. Org. Chem. 2006, 71, 5737;
4. d) S. Bräse, S. Höfener, Angew. Chem. 2005, 117, 8091; Angew. Chem. Int. Ed. 2005, 44, 7879;
5. e) C. L. Hill, M. McGrath, T. Hunt, G. Grogan, Synlett 2006, 309;
6. f) A. Hajra, N. Yoshikai, E. Nakamura, Org. Lett. 2006, 8, 4153;
7. g) J. A. Marshall, M. Herold, H. S. Eidam, P. Eidam, Org. Lett. 2006, 8, 5505;
8. h) D. Huang, J.-X. Wang, Synlett 2007, 2272;
9. i) M. K. Brown, T. L. May, C. A. Baxter, A. H. Hoveyda, Angew. Chem. 2007,119,1115; Angew. Chem. Int. Ed. 2007, 46,1097;
10. j) A. Rimkus, N. Sewald, Org. Lett. 2002, 4, 3289;
11. k) A. Rimkus, N. Sewald, Synthesis 2004, 135;
12. l) N. Maezaki, H. Sawamoto, T. Suzuki, R. Yoshigami, T. Tanaka, J. Org. Chem. 2004, 69, 8387;
13. m) I. H. Escher, A. Pfaltz, Tetrahedron 2000, 56, 2879;
14. n) B. H. Lipshutz, M. R. Wood, R. Tirado, Org. Synth. 1999, 76, 252;
15. o) M. P. Sibi, S. Manyem, Tetrahedron 2000, 56, 8033.
16. a) S. Matsubara, D. Arioka, K. Utimoto, Synlett 1999, 1253;
17. b) S. Matsubara, H. Yamamoto, D. Arioka, K. Utimoto, K. Oshima, Synlett 2000, 1202.
18. a) K. Takai, T. Kakiuchi, Y Kataoka, K. Utimoto, J. Org. Chem. 1994, 59, 2668;
19. b) S. Matsubara, J. Synth. Org. Chem. Jpn. 2000, 58, 118;
20. c) S. Matsubara, K. Oshima, K. Utimoto, J. Organomet. Chem. 2001, 617-618, 39;
21. d) S. Matsubara in The Chemistry of Organozinc Compounds Part2 (Eds.: Z. Rappoport, I. Marek), Wiley, Hoboken, NJ, 2006, Chap. 14, p. 641.
22. a) K. Ukai, K. Oshima, S. Matsubara, J. Am. Chem. Soc. 2000,122, 12047;
23. b) S. Matsubara, K. Ukai, H. Fushimi, Y Yokota, H. Yoshino, K. Oshima, K. Omoto, A. Ogawa, Y Hioki, H. Fujimoto, Tetrahedron 2002, 58, 8255;
24. c) K. Nomura, K. Oshima, S. Matsubara, Tetrahedron Lett. 2004, 45, 5957;
25. d) T. Hirayama, K. Oshima, S. Matsubara, Angew. Chem. 2005, 117, 3357;
26. Angew. Chem. Int. Ed. 2005, 44, 3293;
27. e) K. Nomura, K. Oshima, S. Matsubara, Angew. Chem. 2005, 117, 6010;
28. Angew. Chem. Int. Ed. 2005, 44, 5860;
29. f) K. Nomura, S. Matsubara, Chem. Lett. 2007, 36, 164;
30. g) K. Nomura, K. Asano, T. Kurahashi, S. Matsubara, Heterocycles 2008, 76, 1381.
31. 1H NMR. The same selectivity of (Z)-silyl enol ether formations were also observed when a simple α,β-unsaturated ketone, such as chalcone, was treated with bis(iodozincio)methane in the presence of a silylation reagent.
32. a) T Ibuka, T Nakao, S. Nishii, Y. Yamamoto, J. Am. Chem. Soc. 1986, 108, 7420;
33. b) Y Yamamoto, S. Nishii, T Ibuka, J. Chem. Soc. Chem. Commun. 1987, 464;
34. c)Y Yamamoto, S. Nishii, T Ibuka, J. Chem. Soc. Chem. Commun. 1987, 1572;
35. d) Y Yamamoto, S. Nishii, T Ibuka, J. Am. Chem. Soc. 1988, 110, 617;
36. e) Y Yamamoto, S. Nishii, J. Org. Chem. 1988, 53, 3597;
37. f) T Ibuka, N. Akimoto, M. Tanaka, S. Nishii, Y Yamamoto, J. Org. Chem. 1989, 54, 4055;
38. g) T Ibuka, M. Tanaka, S. Nishii, Y Yamamoto, J. Am. Chem. Soc. 1989, 111, 4864;
39. h) Y Yamamoto, S. Nishii, T Ibuka, J. Chem. Soc. Perkin Trans. 1 1989, 1703;
40. i) Y Yamamoto, Y Chounan, S. Nishii, T Ibuka, H. Kitahara, J. Am. Chem. Soc. 1992, 114, 7652;
41. j) N. Asao, T Shimada, T Sudo, N. Tsukada, K. Yazawa, Y S. Gyoung, T Uye-hara, Y Yamamoto, J. Org. Chem. 1997, 62, 6274;
42. k) Y Chounan, Y Ono, S. Nishii, H. Kitahara, S. Ito, Y Yamamoto, Tetrahedron 2000, 56, 2821.
43. a) E. P. Lodge, C. H. Heathcock, J. Am. Chem. Soc. 1987,109, 3353;
44. b) H. B. Bürgi, J. D. Dunitz, E. Schefter, J. Am. Chem. Soc. 1973, 95, 5065;
45. c) H. B. Bilrgi, J. D. Dunitz, J. M. Lehn, G. Wipff, Tetrahedron 1974, 30, 1563;
46. d) H. B. Bilrgi, J. D. Dunitz, Acc. Chem. Res. 1983, 16, 153;
47. e) L. Girard, P. E. Lock, H. E. Amouri, M. J. McGlinchey, J. Organomet. Chem. 1994, 478, 189;
48. f) C. T Wigal, J. R. Grunwell, J. Hershberger, J. Org. Chem. 1991, 56, 3759;
49. g) A. B. Smith III, P. K. Trumper, Tetrahedron Lett. 1988, 29, 443.
50. a) E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1977, 99, 7360;
51. b) E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1983, 105, 651;
52. c) E. Nakamura, H. Oshino, I. Kuwajima, J. Am. Chem. Soc. 1986, 108, 3745;
53. d) E. Nakamura, J. Shimada, I. Kuwajima, Organometallics 1985, 4, 641;
54. e) E. Nakamura, K. Sekiya, I. Kuwajima, Tetrahedron Lett. 1987, 28, 337;
55. f) I. Kuwajima, E. Nakamura, Top. Curr. Chem. 1990, 155, 1.
56. a) E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1984, 106, 3368;
57. b) E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1986, 27, 83;
58. c) E. Nakamura, S. Aoki, K. Sekiya, H. Oshino, I. Kuwajima, J. Am. Chem. Soc. 1987, 109, 8056;
59. d) S. Aoki, T Fujimura, E. Nakamura, I. Kuwajima, J. Am. Chem. Soc. 1988, 110, 3296;
60. e) S. Aoki, E. Na- kamura, I. Kuwajima, Tetrahedron Lett. 1988, 29, 1541;
61. f) S. Aoki, T Fujimura, E. Nakamura, I. Kuwajima, Tetrahedron Lett. 1989, 30, 6541;
62. g) E. Nakamura, I Kuwajima, Org. Synth. 1983, 61.
63. a) A. R. Katritzky, M. Piffl, H. Lang, E. Anders, Chem. Rev. 1999, 99, 665;
64. b) M. Lombardo, S. Licciulli, C. Trombini, Pure Appl. Chem. 2004, 76, 657;
65. c) R. W. Hoffmann, J. Krüger, D. Brückner, New J. Chem. 2001, 25, 102;
66. d)R. W. Hoffmann, B. Kemper, Tetrahedron Lett. 1981, 22, 5263;
67. e) R. W. Hoffmann, R. Metternich, Liebigs Ann. Chem. 1985, 2390;
68. f) T Moriya, A. Suzuki, N. Miyaura, Tetrahedron Lett. 1995, 36, 1887;
69. g) W. R. Roush, M. R. Michaelides, D. F Tai, B. M. Laser, W. K. M. Chong, D. J. Harris, J. Am. Chem. Soc. 1989, 111, 2984;
70. h)T Hirashita, T Kamei, T Horie, H. Yamamura, M. Kaway, S. Araki, J. Org. Chem. 1999, 64, 172;
71. i) S. Water-lot-Bourdea, J.-L. Parrain, J.-P Quintard, J. Org. Chem. 1999, 64, 172;
72. j) G C. Micalizio, A. N. Pinchuck, W. R. Roush, J. Org. Chem. 2000, 65, 8730;
73. k) G E. Keck, D. E. Abbott, M. R. Wiley, Tetrahedron Lett. 1987, 28, 139;
74. l) Y Yamamoto, K. Komatsu, K. Maruyama, J. Organomet. Chem. 1985, 31, 285;
75. m) S. Jiang, G. E. Agoston, T Chen, M. P. Cabal, E. Turos, Organometallics 1995, 14, 4697;
76. n) K. Takai, K. Nitta, K. Utimoto, Tetrahedron Lett. 1988, 29, 5263;
77. o) W. R. Roush, T D. Bannister, M. D. Wendt, J. A. Jablonowski, K. A. Scheidt, J. Org. Chem. 2002, 67, 4275;
78. p) J.-I. Chika, H. Takei, Tetrahedron Lett. 1998, 39, 605;
79. q) J. A. Marshall, Chem. Rev. 1996, 96, 31;
80. r) J. A. Marshall, K W. Hinkle, J. Org. Chem. 1996, 61, 105;
81. s) W. R. Roush, M. S. Van Nieuwenhze, J. Am. Chem. Soc. 1994, 116, 8536;
82. t) G. E. Keck, K. A. Savi, E.N. Cressman, D. E. Abbott, J. Org. Chem. 1994, 59, 7889;
83. u) I. Kadota, K. Kobayashi, H. Okano, N. Asao, Y Yamamoto, Bull. Soc. Chim. Fr. 1995, 132, 615;
84. v) J. Cossy, C Willis, V. Bellosta, L. Saint-Jalmes, Synthesis 2002, 951;
85. w) H. C Brown, P. K. Jadhav, K. S. Bhat, J. Am. Chem. Soc. 1988, 110, 1535;
86. x) J. A. Hunt, W R. Roush, J. Org. Chem. 1997, 62, 1112.
87. a) S. E. Denmark, J. Fu, Chem. Rev. 2003, 103, 2763;
88. b) G. Sklute, D. Amsallem, A. Shabli, J. P. Varghese, I. Marek, J. Am. Chem. Soc. 2003, 125, 11776;
89. c) G. Sklute, I. Marek, J. Am. Chem. Soc. 2006, 128, 4642;
90. d) R. W Hoffmann, A. Schlapbach, Liebigs Ann. Chem. 1991, 1203.
91. max = 54.0°, R = 0.051 for 6267 reflections (I>2σ(I)).