Asymmetric cyclopropanation of olefins with diazoacetate using chiral copper catalysts

Tetrahedron

Volumn 53, Issue 28, 1997, Pages 9599-9610

  Ichiyanagi, Tsuyoshi ^a   Shimizu, Makoto ^a   Fujisawa, Tamotsu ^a  

^a MIE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZONITRILE; COPPER COMPLEX; CYCLOPROPANE; LIGAND; PHENYLGLYCINE; STYRENE; STYRENE DERIVATIVE;

ARTICLE; CAPILLARY GAS CHROMATOGRAPHY; CATALYST; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030744464     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00644-3     Document Type: Article

References (38)

1. a) Salaün, J. Chem. Rev. 1989, 89, 1247-1270.
2. b) Doyle, M. P. Chem. Rev. 1986, 86, 919-939.
3. c) Doyle, M. P. Recl. Trav. Chim. Pay-Bas 1991, 110, 305-316.
4. a) Nozaki, H.; Moriuchi, S.; Takaya, H.; Noyori, R. Tetrahedron Lett. 1966, 5239-5242.
5. b) Nozaki, H.; Moriuchi, S.; Takaya, H.; Noyori, R. Tetrahedron 1968, 24, 3655-3669.
6. Copper catalyzed asymmetric cyclopropanation; a) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1975, 1707-1710.
7. b) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1977, 2599-2602.
8. c) Aratani, T. Pure Appl. Chem. 1985, 57, 1839-1844.
9. d) Aratani, T.; Yoneyoshi, Y.; Nagase, T. Tetrahedron Lett. 1982, 23, 685-688.
10. e) Müller, D.; Umbricht, G.; Weber, B.; Pfaltz, A. Helv. Chim. Acta 1991, 74, 232-240.
11. f) Leutengger, U.; Umbricht, G. Fahrni, C.; von Matt, P.; Pfaltz, A. Tetrahedron 1992, 48, 2143-2156.
12. g) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005-6008.
13. h) Ito, K.; Katuki, T. Tetrahedron Lett. 1993, 34, 2661-2664.
14. i) Ito, K.; Katuki, T. Synlett 1993, 638-640.
15. j) Ito, K.; Katuki, T. Chem. Lett. 1994, 1857-1859.
16. k) Kanemasa, S.; Hamura, S.; Harada, E.; Yamamoto, H. Tetrahedron Lett. 1994, 35, 7985-7988.
17. l) Gant, T. G.; Noe, M. C.; Corey, E. J. Tetrahedron Lett. 1995, 36, 8745-8748.
18. m) Austin, R. E.; Dalmann, C. J.; Muller, P. J. Am. Chem. Soc. 1991, 113, 1423-1424.
19. n) Abram, D. M. H.; Zhou, Z. J. Chem. Soc. Chem. Commun. 1984, 1038-1040.
20. o) Dammast, F.; Reißig, H. -U. Chem. Ber. 1993, 126, 2449-2456. and the references sited therein.
21. a) Doyle, M. P.; Protopopova, M. N.; Pouller, C. D; Rogers, D. H. J. Am. Chem. Soc. 1995, 117, 7281-7282.
22. b) Doyle, M. P.; Kalinin, A. V. Tetrahedron Lett. 1996, 37, 1371-1374.
23. Fukuda, T; Katsuki, T. Synlett 1995, 825-826.
24. Nishiyama, H.; Itoh, Y.; Matsumoto, H.; Park, S. -B.; Itoh, K. J. Am. Chem. Soc. 1994, 116, 2223-2224.
25. Fritschi, H.; Leutenegger, U.; Pfaltz, A. ; Keller, W.; Kratky, C. Helv. Chim. Acta 1988, 71, 1553-1565.
26. Evans, D. A.; Woerpel, K. A.; Hinmann, M. M.; Faul, M. M. J. Am. Chem. Soc. 1991, 113, 726-728.
27. Fujisawa, T.; Ichiyanagi, T.; Shimizu, M. Tetrahedron Lett. 1995, 36, 5031-5034.
28. a) Dawson, G. J.; Frost, C. G.; Williams, J. M. J. Tetrahedron Lett. 1993, 34, 3149-3152.
29. b) Allen, J. V.; Dawson, G. J.; Frost, C. G.; Williams, J. M. J.; Coote, S. J. Tetrahedron 1994, 50, 799-808.
30. Fritschi, H.; Leutenegger, U.; Siegmann, K.; Pfaltz, A. Helv. Chim. Acta 1988, 71, 1541-1552.
31. In the reaction of 3-acryloyl-1,3-oxazolidin-2-one and cyclopentadiene, the use of chiral ligand 1a gave the 2R-cycloadduct but the use of Tf derivative le gave the 2S-adduct predominantly. (formula presented) Ichiyanagi, T.; Shimizu, M.; Fujisawa, T. J. Org. Chem. submitted for publication.
32. Nakamura, A.; Konishi, A.; Tsujitani, R.; Kudo, M.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3449-3461.
33. Salomon, R. G.; Kochi, J. K. J. Am. Chem. Soc. 1973, 95, 3300-3310.
34. Regitz, M; Maas, G. Diazo Compounds; Academic press: New York, 1986.
35. Regitz, M.; Hocker, J.; Liedhegener, A. Org. Synth. 1973, Col. vol. 5, 179-183.
36. 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, 1906-1912.
37. McKennon, M. J.; Meyers, A. I.; Dranz, K. Schwarm, M. J. Org. Chem. 1993, 58, 3568-3571.
38. Nakamura, A.; Konishi, A.; Tatsuno, Y.; Otsuka, S. J. Am. Chem. Soc. 1978, 100, 3443-3448.