In- or In(I)-employed tailoring of the stereogenic centers in the Reformatsky-type reactions of simple ketones, á-alkoxy ketones, and β-keto esters

Journal of Organic Chemistry

Volumn 70, Issue 25, 2005, Pages 10408-10419

  Babu, Srinivasarao Arulananda ^a   Yasuda, Makoto ^a   Shibata, Ikuya ^a   Baba, Akio ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHELATION; DERIVATIVES; ESTERS; ORGANIC SOLVENTS; REACTION KINETICS; SINGLE CRYSTALS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

CYCLIC TRANSITIONS; HIGH ANTI SELECTIVITY; REFORMATSKY-TYPE REACTIONS; X-RAY STRUCTURE ANALYSIS;

KETONES;

ESTER DERIVATIVE; HALOGEN; INDIUM; KETONE DERIVATIVE; METAL; SOLVENT; TETRAHYDROFURAN; TOLUENE;

ARTICLE; CHELATION; CRYSTAL STRUCTURE; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REFORMATSKY REACTION; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 28744445551     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051659w     Document Type: Article

References (76)

1. Reformatsky, S. Chem. Ber. 1887, 20, 1210.
2. For recent reviews on Reformatsky reactions, see: (a) Fürstner. A. Synthesis 1989, 571.
3. (b) Rathke, M. W.; Weipert, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; New York, 1991; Vol. 2, p 277.
4. (c) Ocampo, R.; Dolbier, W. R., Jr. Tetrahedron 2004, 60, 9325.
5. (d) Orsini, F.; Selb, G. Curr. Org. Synth. 2004, 1, 111.
6. (a) Rieke, R. D.; Uhm, S. J. Synthesis 1975, 452.
7. (b) Santaniello, E.; Manzocchi, A. Synthesis 1977, 698.
8. (c) Csuk, R.; Fürstner, A.; Weidmann, H. J. Chem. Soc., Chem Commun. 1986, 775.
9. (d) Burkhardt, E.; Rieke, R. D. J. Org. Chem. 1985, 50, 416.
10. (e) Inaba, S.-I.; Rieke, R. D. Tetrahedron Lett. 1985, 26, 155.
11. (f) Imamoto, T.; Kusumoto, T.; Tawarayama, Y.; Sugiura, Y.; Mita, T.; Hatanaka, Y.; Yokoyama, M. J. Org. Chem. 1984, 49, 3904.
12. (g) Moriwake, T. J. Org. Chem. 1966, 31, 983.
13. (h) Borno, A.; Bigley, D. B. J. Chem. Soc., Perkin Trans. 2 1983, 1311.
14. Paresh, J. D.; Shelton, D. R.; Little, R. D. Org. Lett. 2003, 5, 3615.
15. (j) Shibata, I.; Suwa, T.; Sakakibara, H.; Baba, A. Org. Lett. 2002, 4, 301 and references therein.
16. For reviews on indium reagents, see: (a) Cintas, P. Synlett 1995, 1087.
17. (b) Podlech, J.; Maier, T. C. Synthesis 2003, 633.
18. (c) Nair, V.; Ros, S.; Jayan, C. N.; Pillai, B.; S. Tetrahedron 2004, 60, 1959.
19. (d) Araki, S.; Hirashita, T. Main Group Metals Org. Synth. 2004, 1, 323.
20. (e) Chan, T. H.; Li, C.-J.; Lee, M. C.; Wei, Z. Y. Can. J. Chem. 1994, 72, 1181.
21. (f) Loh, T.-P. Sci. Synth. 2004, 7, 413.
22. (g) Babu, S. A. Synlett 2002, 531.
23. (h) Fringuelli, F.; Piermatti, O.; Pizzo, F.; Vaccaro, L. Curr. Org. Chem. 2003, 7, 1661.
24. Babu, G.; Perumal, P. T. Aldrichim. Acta 2000, 33, 16.
25. (j) Chauhan, K. K.; Frost, C. G. J. Chem. Soc., Perkin Trans. 1 2000, 3015.
26. (k) Ranu, B. C. Eur. J. Org. Chem. 2000, 2347.
27. (l). Li, C. J.; Chan, T. H. Tetrahedron 1999, 55, 1149.
28. Peppe, C. Curr. Org. Synth. 2004, 1, 227.
29. (a) Kanai, K.; Wakabayashi, H.; Honda, T. Org. Lett. 2000, 2, 2549, and references therein.
30. (b) Aoyagi, Y.; Tanaka, W.; Ohta, A. J. Chem. Soc, Chem. Commun. 1994, 1225.
31. (c) Delaunay, J.; Orliac-Le Moing, A.; Simonet, J. Tetrahedron 1988, 44, 7089.
32. (d) Canceill, J.; Basselier, J. J.; Jacques, J. Bull. Soc. Chim. Fr. 1967, 1024.
33. Ross, N. A.; Bartsch, R. A. J. Org. Chem. 2003, 68, 360 and references therein.
34. For some recent papers, see: (a) Yasuda, M.; Yamasaki, S.; Onishi, Y.; Baba, A. J. Am. Chem. Soc. 2004, 126, 7186.
35. (b) Loh, T.-P.; Yin, Z.; Song, H.-S.; Tan, K.-L. Tetrahedron Lett. 2003, 44, 911.
36. (c) Yi, X.-H.; Meng, Y.; Li, C.-J. J. Chem. Soc, Chem. Commun. 1998, 449.
37. (d) Hirashita, T.; Kamei, T.; Satake, M.; Horie, T.; Shimizu, H.; Araki, S. Org. Biomol. Chem. 2003, 1, 3799.
38. (d) Babu, S. A.; Yasuda, M.; Shibata, I., Baba, A. Synlett 2004, 1223.
39. (e) Paquette, L., A. Synthesis 2003, 765.
40. (f) Kumar, S. Kaur, P. Tetrahedron Lett. 2004, 45, 3413.
41. (g) Vilaivan, T.; Winotapan, C.; Banphavichit, V.; Shinada, T.; Ohfune, Y. J. Org. Chem. 2005, 70, 3464.
42. (h) Khan, F. A.; Dash, J. E. J. Org. Chem. 2004, 2692.
43. For early works dealing with nondiastereoselective Reformatsky-type reactions, see: (a) Chao, L.-C.; Rieke, R. D. J. Org. Chem. 1975, 40, 2253.
44. (b) Nair, V.; Jayan, C. N.; Ros, S. Tetrahedron 2001, 57, 9453.
45. (c) Araki, S.; Ito, H.; Butsugan, Y. Synth. Commun. 1988, 18, 453.
46. (d) Araki, S.; Katsumura, N.; Kawasaki, K.J.; Butsugan, Y. J. Chem. Soc., Perkin Trans. 1 1991, 499.
47. (e) Schick, H.; Ludwig, R.; Schwarz, K.-H.; Kleiner, K.; Kunath, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1191.
48. (f) Araki, S.; Katsumura, N.; Kawasaki, K.; Butsugan, Y. J. Chem. Soc., Perkin Trans, l 1991, 499.
49. (g) Yi, X.-H.; Meng, Y.; Li, C.-J. Tetrahedron Lett. 1997, 38, 4731.
50. Preliminary report: Babu, S. A.; Yasuda, M.; Shibata, I.; Baba, A. Org. Lett. 2004, 6, 4475.
51. (a) Reported yield for this reaction is 99% (ds 3:2) using HIU (20 kHz, 600 W, 13 mm tip diameter at a power level of 7); see ref 6. (b) In some of the cases, InBr was employed. The results are comparable with indium metal as noted in our preliminary studies; see ref 9.
52. (c) The reactions were carried out using method A.
53. Yasuda, M.; Hirata, K.; Nishino, M.; Yamamoto, A.; Baba, A. J. Am. Chem. Soc. 2002, 124, 13442.
54. Vedejs, E.; Daugulis, O. J. Org. Chem. 1996, 61, 5702.
55. Yasuda, M.; Okamoto, K.; Sako, T.; Baba, A. Chem. Commun. 2001, 157 and references therein.
56. For selective reactions under the chelation-controlled conditions, see: (a) Reetz, M. T. Acc. Chem. Res. 1993, 26, 462.
57. (b) Reetz, M. T. Angew. Chem. Int. Ed. Engl. 1994, 23, 556. For the chelation-controlled aldol-type additions to α-alkoxy aldehydes using enol silanes, see:
58. (c) Reetz, M. T.; Kesseler, K.; Jung, A. Tetrahedron 1984, 40, 4327.
59. (d) Reetz, M. T.; Raguse, B.; Marth, C. F.; Hugel, H. M.; Bach, T.; Fox, D. N. A. Tetrahedron 1992, 48, 5731.
60. (e) Reetz, M. T.; Fox, D. N. A. Tetrahedron Lett. 1993, 34, 1119.
61. Picotin, G.; Miginiac, P. J. Org. Chem. 1987, 52, 4796.
62. 2-mediated Reformatsky-type reactions: (a) Orsini, F.; Lucci, E. M. Tetrahedron Lett. 2005, 46, 1909 and references therein.
63. (b) Molander, G. A.; Etter, J. B.; Hairing, L. S.; Thorel, P.-J. Acc. Chem. Res. 1991, 113, 8036.
64. 3; see: Cotton, F. A.; Wilkinson, G.; Murillo, C. A.; Bochmann, M. Advanced Inorganic Chemistry; Wiley: New York, 1999; p 203.
65. Sato, K.; Kira, M.; Sakurai, H. J. Am. Chem. Soc. 1989, 111, 6429.
66. 4 (6 mmol) for 1 mmol of substrate at room temperature.
67. The complete isolation of isomers and the determination of isomeric ratio is under investigation on the stereoselective construction of three subsequent stereogenic centers.
68. 1 NMR spectra see ref 9 and the Supporting Information therein.
69. Similar results have been discussed by Chan et al. for the generation of allyl- or allenylindiums from indium metal and allyl- or propargyl bromide, respectively, in DMF solution, see: (a) Chan, T. H.; Yang, Y. J. Am. Chem. Soc. 1999, 121, 3228.
70. 2 from allyl iodide and In(I)I in THF solution; see:
71. (c) Araki, S.; Ito, H.; Katsumura, N.; Butsugan, Y. J. Organomet. Chem. 1989, 369, 291.
72. Araki, S.; Ito, H.; Butsugan, Y. J. Org. Chem. 1988, 53, 1831.
73. (a) A similar trend was observed in THF as noted in ref 9.
74. 3 also afforded a similar type of spectra and species (see the Supporting Information for the spectra).
75. 3 as well as InCl systems. See the Supporting Information for the spectra.
76. Balsamo, A.; Barili, P., L.; Crotti, P.; Ferretti, M.; Macchia, B.; Macchia, F. J. Chem. Soc., Perkin Trans, 1 1974, 2548.