High Enantioselectivity in the Intramolecular Cyclopropanation of Allyl Diazoacetates Using a Novel Rhodium(II) Catalyst

Journal of the American Chemical Society

Volumn 113, Issue 4, 1991, Pages 1423-1424

  Doyle, Michael P ^a   Pieters, Roland J ^a   Martin, Stephen F ^b   Austin, Richard E ^b   Oalmann, Christopher J ^b   Müller, Paul ^c  

^a TRINITY UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^c UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001733040     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00004a059     Document Type: Article

References (51)

1. Nutting, W. H.; Rappoport, H.; Machlis, L. J. Am. Chem. Soc. 1968, 90, 6434.
2. Connor, D. T.: Greenough, R. C.; von Strandtmann, M. J. Org. Chem. 1977, 42, 3664.
3. Arlt, D.; Jautelat, M.; Lantzsch, R. Angew. Chem., Int. Ed. Engl. 1981, 20, 703.
4. Freer, A. A.; Gardner, D.; Greatbanks, D.; Poyser, J. P. J. Chem. Soc., Chem. Commun. 1982, 1160.
5. Nagaoka, H.; Miyaoka, H.; Yamada, Y. Tetrahedron Lett. 1990, 31, 1573.
6. Kim, G.; Chu-Moyer, M. Y.; Danishefsky, S. J. J. Am. Chem. Soc. 1990, 112, 2003.
7. Wender, P. A.; McDonald, F. E. J. Am. Chem. Soc. 1990, 112, 4956.
8. Arlt, D.; Jautelat, M.; Lantzsch, R. Angew. Chem., Int. Ed. Engl. 1981, 20, 703.
9. James, N. F., Ed. In Recent Advances in the Chemistry of Insect Control; Royal Society of Chemistry: London, 1985; pp 26, 73, 133.
10. Lin, H. W.; Walsh, C. T. Biochemistry of the Cyclopropyl Group. In The Chemistry of the Cyclopropyl Group; Patai, S., Rappoport, Z., Eds.; Wiley: New York, 1987; Chapter 16.
11. Stammer, C. H. Tetrahedron 1990, 46, 2231.
12. Martin, S. F.; Austin, R. E.; Oalmann, C. J. Tetrahedron Lett. 1990, 31, 4731.
13. Griller, D.; Ingold, K. U. Acc. Chem. Res. 1980, 13, 317.
14. Suckling, C. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 537.
15. Suckling, C. J. Spec. Publ.—R. Soc Chem. 1988, No. 65, 128.
16. Hudlicky, T.; Kutchan, T. M.; Naqvi, S. M. Org. React. (N.Y.) 1985, 33, 247.
17. Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
18. Salaün, J. Chem. Rev. 1989, 89, 1247.
19. Doyle, M. P. Chem. Rev. 1986. 86, 919.
20. Maas, G. Top. Curr. Chem. 1987, 137, 75.
21. Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1975, 1707.
22. Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1977, 2599.
23. Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1982, 23, 685.
24. Aratani, T. Pure Appl. Chem. 1985, 57, 1839.
25. Fritschi, H.; Leutenegger, U.; Pfaltz, A. Angew. Chem., Int. Ed. Engl. 1986, 25, 1005.
26. Fritschi, H.; Leutenegger, U.; Siegmann, K.; Pfaltz, A.; Keller, W.; Kratky, C. Helv. Chim. Acta 1988, 71, 1541.
27. Fritschi, H.; Leutenegger, U.; Pfaltz, A. Helv. Chim. Acta 1988, 71, 1553.
28. Pfaltz, A. Mod. Synth. Methods 1989, 5, 199.
29. Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
30. Nozaki, H.; Moriuti, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 5239.
31. Nozaki, H.; Takaya, H.; Moriuti, S.; Noyori, R. Tetrahedron 1968, 24, 3655.
32. Tatsumo, Y.; Konishi, A.; Nakamura, A.; Otsuka, S. J. Chem. Soc., Chem. Commun. 1974, 588.
33. Nakamura, A.; Konishi, A.; Tsujitani, R.; Kudo, M.; Otsuka, S. J. Am. Chem. Soc 1978, 100, 3449.
34. Nakamura, A.; Konishi, A.; Tatsuno, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3443, 6544.
35. Matlin, S. A.; Lough, W. J.; Chan, L.; Abram, D. M. H.; Zhou, Z. J. Chem. Soc., Chem. Commun. 1984, 1038.
36. Daniewski, A. R.; Kowalczyk-Przewloka, T. Tetrahedron Lett. 1982, 23, 2411.
37. Daniewski, A. R.; Kowalczyk-Przewloka, T. J. Org. Chem. 1985, 50, 2976.
38. Brunner, H.; Kluschanzoff, H.; Wutz, K. Bull. Soc. Chim. Belg. 1989, 98, 63.
39. Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Chem. Soc., Chem. Commun. 1990, 361.
40. Doyle, M. P.; Brandes, B.; Kazala, A. P.; Pieters, R. J.; Jarstfer, M. B.; Watkins, L. M.; Eagle, C. T. Tetrahedron Lett. 1990, 31, 6613.
41. Doyle, M. P.; Bagheri, V.; Wandless, T. J.; Harn, N. K.; Brinker, D. A.; Eagle, C. T.; Loh, K.-L. J. Am. Chem. Soc. 1990, 112, 1906.
42. The rhodium(II) complexes 1 and 2 were prepared according to the procedure in ref 17 and were purified by flash chromatography on reverse phase, Baker-CN support.
43. Dennis, A. M.; Korp, J. D.; Bernai, I.; Howard, R. A.; Bear, J. L. Inorg. Chem. 1983, 22, 1522.
44. Ahsan, M. Q.; Bemal, I.; Bear, J. L. Inorg. Chem. 1986, 25, 260.
45. In support of this assignment, two NMR signals for the proton at the 5-position of Rh2(MEPY)4, either 55 or 5R, are observed (δ 4.35, dd, J = 8.7, 2.8 Hz and 4.05, d, J = 6.9 Hz). The methoxy resonance for Rh2(MEPY)4 consists of two singlets at 6 3.73 and 3.70. The trans isomer, which has C2 symmetry, is expected to exhibit only one absorption for each of these protons. Further support of this assignment is provided by the 13C NMR spectrum of 1, which displays two signals for each carbon.
46. Corey, E. J.; Myers, A. G. Tetrahedron Lett. 1984, 25, 3559.
47. Schotten, T.; Boland, W.; Jaenicke, L. Tetrahedron Lett. 1986, 27, 2349.
48. Mukaiyama, T.; Yamashita, H.; Asami, M. Chem. Lett. 1983, 385.
49. Jakovac, I. J.; Jones, J. B. J. Org. Chem. 1979, 44, 2165.
50. Lynch, V. M.; Austin, R. E.; Martin, S. F.; George, T. Acta Crystallogr., in press.
51. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238 and references therein.