Ruthenium Complex-Catalyzed Reaction of Isocyanoacetate and N-Sulfonylimines: Stereoselective Synthesis of N-Sulfonyl-2-Imidazolines

Journal of Organic Chemistry

Volumn 62, Issue 6, 1997, Pages 1799-1803

  Lin, Ying Rui ^a   Zhou, Xiao Ti ^a   Dai, Li Xin ^a   Sun, Jie ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001353802     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961598p     Document Type: Article

References (71)

1. (a) Potts, K. T. In Comprehensive Heterocyclic Chemistry; Katritzky, A., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 5, p 457.
2. (b) Grimmett, M. R. Adv. Heterocycl. Chem. 1980, 27, 241.
3. (c) Volkmann, R. A. In Comprehensive Organic Sythesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 1, p 355.
4. (a) Hoppe, D.; Schollkopf, U. Liebigs. Ann. Chem. 1972, 763, 1.
5. (b) Matsumoto, K.; Ozaki, Y.; Suzuki, M.; Miyoshi, M. Agric. Biol. Chem. 1976, 40, 2045.
6. (c) Matsumoto, K.; Urabe, Y.; Ozaki, Y.; Iwasaki, T.; Miyoshi, M. Agric. Biol. Chem. 1975, 39, 1869.
7. Naota, T.; Taki, H.; Mizuno, M.; Murahashi, S-I. J. Am. Chem. Soc. 1989, 111, 5954.
8. Lin, Y.-R.; Zhu, X.-C.; Xiang, M. J. Organomet. Chem. 1993, 448, 215
9. (a) Slough, G. A.; Bergman, R. G.; Heathcock, C. H. J. Am. Chem. Soc. 1989, 111, 938.
10. (b) Burkhardt, E. R.; Doney, J. J.; Slough, G. A.; Stack, J. M.; Heathcock, C. H.; Bergman, R. G. Pure. Appl Chem. 1988, 60, 1.
11. (c) Mizuho, Y.; Kasuga, N.; Komiya, S. Chem. Lett. 1991, 2127.
12. (d) Hirano, M.; Ito, Y.; Hirai, M.; Fukuoka, A.; Komiya, S. Chem. Lett. 1993, 2057.
13. (e) Paganelli, S.; Schionato, A.; Botteghi, C. Tetrahedron Lett. 1988. 32. 2807.
14. (f) Shida, N.; Kubota, Y.; Fukui, H.; Asao, N.; Kadota, I.; Yamamoto, Y. Tetrahedron Lett. 1995, 36, 5023.
15. (g) Yamamoto, Y.; Kubota, Y.; Honda, Y.; Fukui, H.; Asao, N.; Nemoto, H. J. Am. Chem. Soc. 1994, 116, 3161.
16. (a) Ito, Y.; Matsuura, T.; Saeguse, T. Tetrahedron Lett. 1985, 26, 5781.
17. (b) Saeguse, T.; Ito, Y.; Kinoshita, H.; Tomita, S. J. Org. Chem. 1971, 36, 3316.
18. (c) Heinzer, F.; Bellus, D. Helv. Chim. Acta 1981, 64, 2279.
19. For general reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993. (b) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (c) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emure, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (e) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935. (f) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727. (g) Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073. (h) Soloshonok, v. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245. (i) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
20. For general reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993. (b) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (c) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emure, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (e) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935. (f) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727. (g) Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073. (h) Soloshonok, v. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245. (i) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
21. For general reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993. (b) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (c) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emure, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (e) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935. (f) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727. (g) Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073. (h) Soloshonok, v. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245. (i) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
22. For general reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993. (b) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (c) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emure, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (e) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935. (f) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727. (g) Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073. (h) Soloshonok, v. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245. (i) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
23. For general reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993. (b) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (c) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emure, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (e) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935. (f) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727. (g) Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073. (h) Soloshonok, v. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245. (i) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
24. For general reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993. (b) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (c) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emure, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (e) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935. (f) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727. (g) Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073. (h) Soloshonok, v. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245. (i) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
25. For general reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993. (b) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (c) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emure, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (e) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935. (f) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727. (g) Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073. (h) Soloshonok, v. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245. (i) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
26. For general reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993. (b) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (c) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emure, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (e) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935. (f) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727. (g) Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073. (h) Soloshonok, v. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245. (i) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
27. For general reviews: (a) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH Publishers: New York, 1993. (b) Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405. (c) Ito, Y.; Sawamura, M.; Hayashi, T. Tetrahedron Lett. 1987, 28, 6215. (d) Ito, Y.; Sawamura, M.; Hamashima, H.; Emure, T.; Hayashi, T. Tetrahedron Lett. 1989, 30, 4681. (e) Sawamura, M.; Hamashima, H.; Ito, Y. J. Org. Chem. 1990, 55, 5935. (f) Sawamura, M.; Nakayama, Y.; Kato, T.; Ito, Y. J. Org. Chem. 1995, 60, 1727. (g) Hundscheid, F. J. A.; Tandon, V. K.; Rouwette, P. H. F. M.; van Leusen, A. M. Tetrahedron 1987, 43, 5073. (h) Soloshonok, v. A.; Kacharov, A. D.; Hayashi, T. Tetrahedron 1996, 52, 245. (i) Togni, A.; Pastor, S. D. J. Org. Chem. 1990, 55, 1649.
28. For the base-promoted aldol reaction: (a) Meyer, R.; Schîllkopf, U.; Bîhme, P. Liebigs. Ann. Chem. 1977, 1183. (b) Van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153.
29. For the base-promoted aldol reaction: (a) Meyer, R.; Schîllkopf, U.; Bîhme, P. Liebigs. Ann. Chem. 1977, 1183. (b) Van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153.
30. Formation of 2-imidazoline has been reported via 1,3-dipolar cycloaddition approach: (a) Bunge, K.; Huisgen, R.; Raab, R.; Sturm, H. J. Chem. Ber. 1972, 105, 1307. (b) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons, Inc.: New York, 1984; Vol. 1, p 177. (c) Muller, F.; Mattay, J. Chem. Ber. 1993, 543. (d) Jackson, B.; Gakis, N.; Marky, M.; Hansen, H. J.; Von Philipsborn, W.; Schmid, H. Helv. Chim. Acta 1972, 55, 916. (e) Jackson, B.; Marky, M.; Hansen, H. J.; Schmid, H. Helv. Chim. Acta 1972, 55, 919. (f) Gilgen, P.; Heimgartner, H.; Schmid, H.; Hansen, H. J. Heterocycles 1977, 6, 143. (g) Bianchi, G.; De Micheli, C.; Gandolfi, R. Angew. Chem., Int. Ed. Engl. 1979, 18, 721.
31. Formation of 2-imidazoline has been reported via 1,3-dipolar cycloaddition approach: (a) Bunge, K.; Huisgen, R.; Raab, R.; Sturm, H. J. Chem. Ber. 1972, 105, 1307. (b) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons, Inc.: New York, 1984; Vol. 1, p 177. (c) Muller, F.; Mattay, J. Chem. Ber. 1993, 543. (d) Jackson, B.; Gakis, N.; Marky, M.; Hansen, H. J.; Von Philipsborn, W.; Schmid, H. Helv. Chim. Acta 1972, 55, 916. (e) Jackson, B.; Marky, M.; Hansen, H. J.; Schmid, H. Helv. Chim. Acta 1972, 55, 919. (f) Gilgen, P.; Heimgartner, H.; Schmid, H.; Hansen, H. J. Heterocycles 1977, 6, 143. (g) Bianchi, G.; De Micheli, C.; Gandolfi, R. Angew. Chem., Int. Ed. Engl. 1979, 18, 721.
32. Formation of 2-imidazoline has been reported via 1,3-dipolar cycloaddition approach: (a) Bunge, K.; Huisgen, R.; Raab, R.; Sturm, H. J. Chem. Ber. 1972, 105, 1307. (b) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons, Inc.: New York, 1984; Vol. 1, p 177. (c) Muller, F.; Mattay, J. Chem. Ber. 1993, 543. (d) Jackson, B.; Gakis, N.; Marky, M.; Hansen, H. J.; Von Philipsborn, W.; Schmid, H. Helv. Chim. Acta 1972, 55, 916. (e) Jackson, B.; Marky, M.; Hansen, H. J.; Schmid, H. Helv. Chim. Acta 1972, 55, 919. (f) Gilgen, P.; Heimgartner, H.; Schmid, H.; Hansen, H. J. Heterocycles 1977, 6, 143. (g) Bianchi, G.; De Micheli, C.; Gandolfi, R. Angew. Chem., Int. Ed. Engl. 1979, 18, 721.
33. Formation of 2-imidazoline has been reported via 1,3-dipolar cycloaddition approach: (a) Bunge, K.; Huisgen, R.; Raab, R.; Sturm, H. J. Chem. Ber. 1972, 105, 1307. (b) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons, Inc.: New York, 1984; Vol. 1, p 177. (c) Muller, F.; Mattay, J. Chem. Ber. 1993, 543. (d) Jackson, B.; Gakis, N.; Marky, M.; Hansen, H. J.; Von Philipsborn, W.; Schmid, H. Helv. Chim. Acta 1972, 55, 916. (e) Jackson, B.; Marky, M.; Hansen, H. J.; Schmid, H. Helv. Chim. Acta 1972, 55, 919. (f) Gilgen, P.; Heimgartner, H.; Schmid, H.; Hansen, H. J. Heterocycles 1977, 6, 143. (g) Bianchi, G.; De Micheli, C.; Gandolfi, R. Angew. Chem., Int. Ed. Engl. 1979, 18, 721.
34. Formation of 2-imidazoline has been reported via 1,3-dipolar cycloaddition approach: (a) Bunge, K.; Huisgen, R.; Raab, R.; Sturm, H. J. Chem. Ber. 1972, 105, 1307. (b) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons, Inc.: New York, 1984; Vol. 1, p 177. (c) Muller, F.; Mattay, J. Chem. Ber. 1993, 543. (d) Jackson, B.; Gakis, N.; Marky, M.; Hansen, H. J.; Von Philipsborn, W.; Schmid, H. Helv. Chim. Acta 1972, 55, 916. (e) Jackson, B.; Marky, M.; Hansen, H. J.; Schmid, H. Helv. Chim. Acta 1972, 55, 919. (f) Gilgen, P.; Heimgartner, H.; Schmid, H.; Hansen, H. J. Heterocycles 1977, 6, 143. (g) Bianchi, G.; De Micheli, C.; Gandolfi, R. Angew. Chem., Int. Ed. Engl. 1979, 18, 721.
35. Formation of 2-imidazoline has been reported via 1,3-dipolar cycloaddition approach: (a) Bunge, K.; Huisgen, R.; Raab, R.; Sturm, H. J. Chem. Ber. 1972, 105, 1307. (b) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons, Inc.: New York, 1984; Vol. 1, p 177. (c) Muller, F.; Mattay, J. Chem. Ber. 1993, 543. (d) Jackson, B.; Gakis, N.; Marky, M.; Hansen, H. J.; Von Philipsborn, W.; Schmid, H. Helv. Chim. Acta 1972, 55, 916. (e) Jackson, B.; Marky, M.; Hansen, H. J.; Schmid, H. Helv. Chim. Acta 1972, 55, 919. (f) Gilgen, P.; Heimgartner, H.; Schmid, H.; Hansen, H. J. Heterocycles 1977, 6, 143. (g) Bianchi, G.; De Micheli, C.; Gandolfi, R. Angew. Chem., Int. Ed. Engl. 1979, 18, 721.
36. Formation of 2-imidazoline has been reported via 1,3-dipolar cycloaddition approach: (a) Bunge, K.; Huisgen, R.; Raab, R.; Sturm, H. J. Chem. Ber. 1972, 105, 1307. (b) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons, Inc.: New York, 1984; Vol. 1, p 177. (c) Muller, F.; Mattay, J. Chem. Ber. 1993, 543. (d) Jackson, B.; Gakis, N.; Marky, M.; Hansen, H. J.; Von Philipsborn, W.; Schmid, H. Helv. Chim. Acta 1972, 55, 916. (e) Jackson, B.; Marky, M.; Hansen, H. J.; Schmid, H. Helv. Chim. Acta 1972, 55, 919. (f) Gilgen, P.; Heimgartner, H.; Schmid, H.; Hansen, H. J. Heterocycles 1977, 6, 143. (g) Bianchi, G.; De Micheli, C.; Gandolfi, R. Angew. Chem., Int. Ed. Engl. 1979, 18, 721.
37. (a) For a review concerning synthesis of 2-imidazoline: Ferm, R. J.; Riebsomer, J. L. Chem. Rev. 1954, 593. (b) Steele, J.; Gough, M. J. In Comprehesive Organic Functional Group Transformations; Katritzky, A., Meth-Cohn, O., Rees, C. W., Kirby, G. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 4, p 537.
38. (a) For a review concerning synthesis of 2-imidazoline: Ferm, R. J.; Riebsomer, J. L. Chem. Rev. 1954, 593. (b) Steele, J.; Gough, M. J. In Comprehesive Organic Functional Group Transformations; Katritzky, A., Meth-Cohn, O., Rees, C. W., Kirby, G. W., Eds.; Pergamon Press: Oxford, 1995; Vol. 4, p 537.
39. During the revision of this manuscript, a gold(I)-catalyzed reaction was reported, see: Hayashi, T.; Kishi, E.; Soloshonok, V. A.; Uozumi, Y. Tetrahedron Lett. 1996, 37, 4969.
40. Zhu, X. Thesis of Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 1991.
41. 55) coupling constant of 11.3 Hz. trans-4,5-disubstituted-2-imidazolines always display smaller vicinal couling constants than do cis isomers. This is in accord with the trans/cis coupling constants for five- membered ring compounds.
42. Ojima, I. Acc. Chem. Res. 1995, 28, 283.
43. (a) Waki, M.; Kitajima, Y.; Izumiya, N. Synthesis. 1981, 266.
44. (b) Kittaka, A.; Sugano, Y.; Otsuka, M.; Ohno, M.; Sugiura, Y.; Umezawa, H. Tetrahedron Lett. 1986, 27, 3631.
45. (c) Sugano, Y.; Kittaka, A.; Ostuka, M.; Ohno, M.; Sugiura, Y.; Umezawa, H. Tetrahedron Lett. 1986, 27, 3635.
46. (d) Ostuka, M.; Kittaka, A.; Ohno, H.; Suzuki, T.; Kuwahara, J.; Sugiura, Y.; Umezawa, H. Tetrahedron Lett. 1986, 27, 3639.
47. (e) Ostuka, M.; Kittaka, A.; Iiomori T.; Yamashita, H., Kobayashi, S.; Ohno, M. Chem. Pharm. Bull. 1985, 33, 509.
48. (a) Baldwin, J. E.; Adlington R. M.; Birch, D. J. Tetrahedron Lett. 1985, 26, 5931.
49. (b) Baldwin, J. E.; Adlington, R. M.; Birch, D. J. J. Chem. Soc., Chem. Commun. 1985, 256.
50. (c) Kiaer, A.; Larsen, P. O. Acta. Chem. Scand. 1959, 13, 1565.
51. Dunn, P. J.; Haner, R.; Rapoport, H. J. Org. Chem. 1990, 55,
52. (18)(a) Tanner D.; Somfai, P. Tetrahedron 1988, 29, 613.
53. (b) Tanner, D.; Somfai P. Tetrahedron. 1988, 29, 619.
54. (c) Southgate, R. Contemp. Org. Synth. 1994, 1(6) 417.
55. (a) Murahashi, S.-I.; Naota, T.; Taki, H.; Mizuno, M.; Takaga, H.; Komiya, S.; Mizuho, Y.; Oyasato, N.; Hiraoka, M.; Hirano, M.; Fukuoka, A. J. Am. Chem. Soc. 1995, 117, 12436.
56. (b) Komiya, S.; Mizuho, Y.; Kasuga, N. Chem. Lett. 1991, 2127.
57. (a) Love, B. E.; Raje, P. S.; Williams, T. C., II Synlett, 1994, 493.
58. (b) Jennings, W. B.; Lovely, C. T. Tetrahedron Lett. 1988, 29, 3725.
59. Hartman, G. D.; Weinstock, L. M. Org. Synth. 1988, 6, 620.
60. Clerici, M. G.; Gioacchino, S. D.; Maspero, F.; Perrotti, E.; Zanobi, A. J. Organomet, Chem. 1975, 84, 379.
61. Ahmad, N.; Levison, J. J.; Robinson, S. D.; Uttley, M. F. Inorg. Synth. 1974, 15, 45.
62. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
63. Kharasch, M. S.; Seyler, R. C.; Mayo, F. R. J. Am. Chem. Soc. 1938, 60, 882.
64. Hayashi, T.; Konishi, M.; Kobori, Y.; Kumada, M.; Higuchi, T.; Hirotsu, K. J. Am. Chem. Soc. 1984, 106, 158.
65. (a) Young, R.; Wilkinson, G. Inorg. Synth. 1977, 17, 75.
66. (b) Harris, R. O.; Hota, N. K.; Sadavoy, L.; Yuen, J. M. C. J. Organomet. Chem. 1973, 54, 259.
67. Peet, W. G.; Gerlach, D. H. Inorg. Synth. 1974, 15, 38.
68. Ukai, T.; Kawazura, H.; Ishii, Y.; Bonnet, J. J.; Ibers, J. A. J. Organomet. Chem. 1974, 65, 253.
69. King, R. B.; Kapoor, P. N. J. Am. Chem. Soc. 1969, 91, 5191.
70. Bishop, J. J.; Davison, A.; Katcher, M. L.; Lichtenberg, D. W.; Merrill, R. E.; Smart, J. C. J. Organomet. Chem. 1971, 27, 241.
71. The author has deposited atomic coordinates for this structure with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK