Diastereoselective Reduction of Cyclopropenylcarbinol: New Access to anti-Cyclopropylcarbinol Derivatives

Organic Letters

Volumn 6, Issue 3, 2004, Pages 341-343

  Zohar, Elinor ^a   Marek, Ilan ^a  

^a TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPENYLCARBINOL; DEUTERIUM; METHANOL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ISOMER; REDUCTION; STEREOCHEMISTRY;

EID: 1342264154     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036143i     Document Type: Article

References (47)

1. Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
2. Hoveyda, A. H.; Evans, D. A.; Fu, G. A. Chem. Rev. 1993, 93, 1307.
3. (a) Ratier, M.; Castaing, M.; Godet, J.-Y.; Pereyre, M. J. Chem. Res., Miniprint 1978, 2309.
4. (b) Schollkopf, U.; Tiller, T.; Bardenhagen, J. Tetrahedron 1988, 44, 5293.
5. (c) Molander, G. A.; Etter, J. B. J. Org. Chem. 1987, 52, 3942.
6. (d) Molander, G. A.; Harring, L. S. J. Org. Chem. 1989, 54, 3525.
7. (e) Lautens, M.; Delanghe, P. H. M. J. Org. Chem. 1992, 57, 798.
8. (f) Lautens, M.; Delanghe, P. H. M. J. Org. Chem. 1995, 60, 2474.
9. (g) Charette, A. B.; Molinaro, C.; Brochu, C. J. Am. Chem. Soc. 2001, 123, 12160.
10. (h) Charette, A. B.; Beauchemin, A. Org. React. 2001, 58, 1.
11. (a) Delanghe, P. H.; Lautens, M. Tetrahedron Lett. 1994, 35, 9513.
12. (b) Kazuta, Y.; Abe, H.; Yamamoto, T.; Matsuda, A.; Shuto, S. J. Org. Chem. 2003, 68, 3511.
13. Charette, A. B.; Lacasse, M.-C. Org. Lett. 2002, 4, 3351.
14. Yang, Z.; Lorenz, J.; Shi, Y. Tetrahedron Lett. 1998, 39, 8621.
15. (a) Groth, U.; Schollkopf, U.; Tiller, T. Liebigs Ann. Chem. 1991, 857.
16. (b) Charette, A. B.; Lemay, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1090.
17. (c) Charette, A. B.; Marcoux, J.-F.; Molinaro, C.; Beauchemin, A.; Brochu, C.; Isabel, E. J. Am. Chem. Soc. 2000, 122, 4508.
18. (d) Shibli, A.; Varghese, J. P.; Knochel, P.; Marek, I. Synlett 2001, 818.
19. (a) Midland, M. M.; Kwon, Y. C. J. Am. Chem. Soc. 1985, 107, 3725.
20. (b) Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487.
21. (c) Heathcock, C. H.; Jarvi, E. T.; Rosen, T. Tetrahedron Lett. 1984, 25, 243.
22. (a) Evans, D. A.; Bartoli, J.; Godel, T. Tetrahedron Lett. 1982, 23, 4577.
23. (b) Nicolaou, K. C.; Pavia, M. R.; Seitz, S. P. J. Am. Chem. Soc. 1982, 104, 2027.
24. (c) Schulte-Elte, K. H.; Ohloff, G. Helv. Chim. Acta 1967, 50, 153.
25. Still, W. C.; Darst, K. P. J. Am. Chem. Soc. 1980, 102, 7387.
26. Cyclopropene derivatives are well-known and were successfully used in synthesis. For recent review, see: (a) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (b) Houben-Weyl, Methods in Organic Chemistry, Carbocyclic Three-Membered Ring Compounds; de Meijere, A., Ed.; Thieme: Stuttgart, Germany, 1997; Vol. E 17d, p 2695. (c) Stoll, A. T.; Negishi, E. Tetrahedron Lett. 1985, 26, 5671.
27. Cyclopropene derivatives are well-known and were successfully used in synthesis. For recent review, see: (a) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (b) Houben-Weyl, Methods in Organic Chemistry, Carbocyclic Three-Membered Ring Compounds; de Meijere, A., Ed.; Thieme: Stuttgart, Germany, 1997; Vol. E 17d, p 2695. (c) Stoll, A. T.; Negishi, E. Tetrahedron Lett. 1985, 26, 5671.
28. Cyclopropene derivatives are well-known and were successfully used in synthesis. For recent review, see: (a) Nakamura, M.; Isobe, H.; Nakamura, E. Chem. Rev. 2003, 103, 1295. (b) Houben-Weyl, Methods in Organic Chemistry, Carbocyclic Three-Membered Ring Compounds; de Meijere, A., Ed.; Thieme: Stuttgart, Germany, 1997; Vol. E 17d, p 2695. (c) Stoll, A. T.; Negishi, E. Tetrahedron Lett. 1985, 26, 5671.
29. Baird, M. S.; Hussain, H. H.; Nethercott, W. J. Chem. Soc., Perkin Trans. 1 1986, 1845.
30. (a) Baird, M. S.; Nethercott, W. Tetrahedron Lett. 1983, 24, 605.
31. (b) Baird, M. S.; Hussain, H. H. Tetrahedron 1987, 43, 215.
32. (c) Al-Dulayymi, J. R.; Baird, M. S. Tetrahedron Lett. 1988, 29, 6147.
33. (d) Al-Dulayymi, J. R.; Baird, M. S. Tetrahedron 1989, 45, 7601.
34. (e) Al-Dulayymi, A. R.; Baird, M. S. J. Chem. Soc., Perkin Trans. 1 1994, 1547.
35. (a) Vincens, M.; Dumont, C.; Vidal, M.; Domnin, I. N. Tetrahedron 1983, 39, 4281.
36. (b) Vidal, M.; Arnaud, P. Bull. Soc. Chim. Fr. 1972, 675.
37. (a) Charette, A. B.; Lebel, H. J. Org. Chem. 1995, 60, 2966.
38. 13C NMR on the crude reaction mixture.
39. The stereospecific formation of diene will be reported in due course.
40. (a) Cox, J. D.; Pilcher, G. Thermochemistry of Organic and Organometallic Compounds; Academic Press: New York, 1970.
41. (b) Gloss, G. Adv. Alicyclic Chem. 1966, 1, 53.
42. (a) Hiyama, T.; Kanamura, A.; Motizawa, Y.; Nozaki, H. Tetrahedron Lett. 1982, 23, 1279.
43. (b) Nakajima, T.; Tanabe, M.; Ohno, K.; Suga, S. Chem. Lett. 1986, 177.
44. (c) Negishi, E.; Takahashi, T. J. Am. Chem. Soc. 1986, 108, 3402.
45. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
46. Houk, K. N.; Rondan, N. G.; Wu, Y.-D.; Metz, J. T.; Paddon-Row, M. N. Tetrahedron 1984, 40, 2257.
47. Carter, F. L.; Frampton, V. L. Chem. Rev. 1964, 64, 497.