Exploring new reactive species for cyclopropanation

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8621-8624

  Yang, Zhiqiang ^a   Lorenz, Jon C ^a   Shi, Yian ^a  

^a Veterinary Dentistry and Oral Surgery   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALKENE; ZINC;

ARTICLE; CHIRALITY; PH; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0032548133     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01954-6     Document Type: Article

References (43)

1. 1 For leading references see: (a) Simmons, H.E.; Smith, R.D. J. Am. Chem. Soc. 1958, 80, 5323.
2. (b) Simmons, H.E.; Smith, R.D. J. Am. Chem. Soc. 1959, 81, 4256.
3. (c) Wittig, G.; Wingler, F. Chem. Ber. 1964, 97, 2146.
4. (d) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron Lett. 1966, 3353.
5. (e) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53.
6. (f) Nishimura, J.; Furukawa, J.; Kawabata, N.; Kitayama, M. Tetrahedron 1971, 27, 1799.
7. (g) Simmons, H.E.; Cairns, T.L.; Vladuchick, S.A.; Hoiness, C.M. Org. React. 1973, 20, 1.
8. (h) Denmark, S.E.; Edwards, J.P.; Wilson, S.R. J. Am. Chem. Soc. 1992, 114, 2592.
9. (i) Hoveyda, A.H.; Evans, D.A.; Fu, G.C. Chem. Rev. 1993, 93, 1307.
10. (j) Charette, A.B.; Marcoux, J-F. Synlett, 1995, 1197.
11. (k) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
12. (l) Charette, A.B.; Marcoux, J-F. J. Am. Chem. Soc. 1996, 118, 4539.
13. (m) Bernardi, F.; Bottoni, A.; Miscione, G.P. J. Am. Chem. Soc. 1997, 119, 12300.
14. 2. For leading references see: (a) Rawson, R.J.; Hanison, I.T. J. Org. Chem. 1970, 35, 2057.
15. (b) Denis, J.M.; Girard, C.; Conia, J.M. Synthesis 1972, 549.
16. (c) Friedrich, E.C.; Lunetta, S.E.; Lewis, E.J. J. Org. Chem. 1989, 54, 2388.
17. (d) Friedrich, E.G.; Lewis, E.J. J. Org. Chem. 1990, 55, 2491.
18. (e) Denmark, S.E.; Edwards, J.P. J. Org. Chem. 1991, 56, 6974.
19. (f) refs. 1h, 1l, and 1m.
20. 4), filtered, concentrated, and purified by column chromatography (hexanes/ether = 50/1) to yield the cyclopropane product (2.61 g, 95.3% ).
21. 4. (a) Mio, S.; Kumagawa, Y.; Sugai, S. Tetrahedron 1991, 47, 2133.
22. (b) Wang, Z-X.; Tu, Y.; Frohn, M.; Zhang, J-R.; Shi, Y. J. Am. Chem. Soc. 1997, 119, 11224.
23. 5. Charette reported that the rate of the intramolecular cyclopropanation for alkoxy (iodomethyl)zinc could be accelerated by adding a Lewis acid. The rate enhancement was attributed to the increased electrophilicity of the methylene group upon complexation. Charette, A.B. Brochu, C. J. Am. Chem. Soc. 1995, 117, 11367.
24. 6. Noltes, J.G.; Boersma, J. J. Organometal. Chem. 1968, 12, 425.
25. 7 (a) Ukaji, Y.; Nishimura, M.; Fujisawa, T. Chem. Lett. 1992, 61.
26. (b) Ukaji, Y.; Sada, K.; Inomata, K. Chem. Lett. 1993, 1227.
27. 8 Denmark, S.E.; Edwards, J.P. Synlett, 1992, 229.
28. 9. (a) Charette, A.B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651.
29. (b) Charette, A.B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081.
30. (c) Charette, A.B.; Juteau, H.; Lebel, H.; Deschenes, D. Tetrahedron Lett. 1996, 37, 7925.
31. (d) Kasdorf, K.; Liotta, D.C. Chemtracts-Organic Chemistry 1997, 10, 533.
32. 10. (a) Kitajima, H.; Aoki, Y.; Ito, K.; Katsuki, T. Chem. Lett. 1995, 1113.
33. (b) Kitajima, H.; Ito, K.; Aoki, Y.; Katsuki, T. Bull. Chem. Soc. Jpn., 1997, 70, 207.
34. 11. (a) Takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett. 1992, 33, 2575.
35. (b) Imai, N.; Takahashi, H.; Kobayashi, S. Chem. Lett. 1994, 177.
36. (c) Imai, N.; Sakamoto, K.; Takahashi, H.; Kobayashi, S. Tetrahedron Lett. 1994, 35, 7045.
37. (d) Takahashi, H.; Yoshioka, M.; Shibasaki, M.; Ohno, M.; Imai, N.; Kobayashi, S. Tetrahedron 1995, 51, 12013.
38. 12. (a) Denmark, S.E.; Christenson, B.L.; Coe, D.M.; O'Connor, S.P. Tetrahedron Lett. 1995, 36, 2215.
39. (b) Denmark, S.E.; Christenson, B.L.; O'Connor, S.P. Tetrahedron Lett. 1995, 36, 2219.
40. (c) Denmark, S.E.; O'Connor, S.P. J. Org. Chem. 1997, 62, 584.
41. (d) Denmark, S.E.; O'Connor, S.P. J. Org. Chem. 1997, 62, 3390.
42. 13. Sawada, S.; Oda, J.; Inouye, Y. J. Org. Chem. 1968, 33, 2141.
43. 14 Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron Lett. 1968, 3495.