Asymmetric intramolecular cyclopropanation of diazo compounds with metallosalen complexes as catalyst: Structural tuning of salen ligand

Tetrahedron Asymmetry

Volumn 14, Issue 7, 2003, Pages 823-836

  Saha, Biswajit ^a   Uchida, Tatsuya ^a   Katsuki, Tsutomu ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALKENYL GROUP; CHEMICAL COMPOUND; COPPER COMPLEX; KETONE DERIVATIVE; LIGAND; RUTHENIUM;

ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CHIRALITY; CYCLIZATION; CYCLOPROPANATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INFRARED SPECTROMETRY; INFRARED SPECTROSCOPY; MOLECULAR DYNAMICS; OPTICAL ROTATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037418794     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00167-8     Document Type: Article

References (54)

1. Doyle M.P., McKervey M.A., Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. 1998;John Wiley & Sons, New York.
2. Doyle M.P., Protopopova M.N. Tetrahedron. 54:1998;7919-7946
3. Pfaltz, A.; Lydon, K. M.; McKervey, A. M.; Charette, A. B.; Level, H. Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A., Eds.; Yamamoto, H. Springer, Berlin, 1999; Chapter 16.
4. Niimi T., Uchida T., Irie R., Katsuki T. Adv. Synth. Catal. 343:2001;79-87.
5. Uchida T., Irie R., Katsuki T. Tetrahedron. 56:2000;3501-3509.
6. Doyle M.P., Peterson C.S., Parker D.L. Jr. Angew. Chem., Int. Ed. Engl. 35:1996;1334-1336.
7. Tokunoh R., Tomiyama H., Sodeoka M., Shibasaki M. Tetrahedron Lett. 37:1996;2449-2452.
8. Müller P.C., Boléa C. Synlett. 2000;826-828.
9. Pique C., Fahndrich B., Pfaltz A. Synlett. 1995;491-492.
10. Cho D.J., Jeon S.-J., Kim H.-S., Cho C.-S., Shim S.-C., Kim T.-J. Tetrahedron: Asymmetry. 10:1999;3833-3848.
11. Park S.-B., Murata K., Matsumoto H., Nishiyama H. Tetrahedron: Asymmetry. 6:1995;2487-2494.
12. Nishiyama H., Itoh Y., Sugawara Y., Matsumoto H., Aoki K., Itoh K. Bull. Chem. Soc. Jpn. 68:1995;1247-1262.
13. Doyle M.P., Austin R.E., Bailey A.S., Dwyer M.P., Dyatkin A.B., Kalinin A.V., Kwan M.M.Y., Liras S., Oalmann C.J., Pieters R.J., Protopopova M.N., Raab C.E., Roos G.H., Zhou Q.-L., Martin S.F. J. Am. Chem. Soc. 117:1995;5763-5765.
14. Doyle M.P., Hu W., Chapman B., Marnett A.B., Peterson C.S., Vitale J.P., Stanley S.A. J. Am. Chem. Soc. 122:2000;5718-5728.
15. Doyle M.P., Davies S.B., Hu W. Org. Lett. 2:2000;1145-1147.
16. Martin S.F., Spaller M.R., Liras S., Hartmann B. J. Am. Chem. Soc. 116:1994;4493-4494.
17. Doyle M.P., Peterson C.S., Se Q.-L., Nishiyama H. J. Chem. Soc., Chem. Commun. 1997;211-212.
18. Davies H.M.L., Brion D.D. Tetrahedron Lett. 37:1996;3967-3970.
19. Davies H.M.L., Brion D.D. J. Org. Chem. 64:1999;8501-8508.
20. Munslow I.J., Gillespie K.M., Deeth R.J., Scott P. Chem. Commun. 2001;1638-1639.
21. Kim G.-S., Cho W.-C., Ahn H.K. Tetrahedron. 55:1999;10079-10086.
22. Park W.-S., Son H.-J., Kim G.-S., Ahn H.K. Tetrahedron: Asymmetry. 10:1999;1903-1911.
23. Che C.-M., Huang J.-S., Lee F.-W., Li Y., Lai T.-S., Kwong H.-L., Teng P.-F., Lee W.-S., Lo W.-C., Peng S.-M., Zhou Z.-Y. J. Am. Chem. Soc. 123:2001;4119-4129.
24. Doyle M.P., Eismont M.Y., Zhou Q.L. Russ. Chem. Bull. 46:1997;955-958.
25. Barberis M., Pérez-Prieto J., Stribia S.-E., Lahuerta P. Org. Lett. 3:2001;3317-3319
26. Barberis, M.; Pérez-Prieto, J.; Herbst, K.; Lahuerta, P. Organometallics 2002, 21, 1667-1673. Although the enantioselectivity of the cyclopropanation giving bicyclo[3.1.0]hexan-2-one has been reported to be 87% in Ref. 15a, it has been reported to be 74% in Ref. 15b.
27. Katsuki T. Adv. Synth. Catal. 34:2002;131-147.
28. For preliminary communication, see: (a) Saha, B.; Uchida, T.; Katsuki, T. Synlett 2001, 114-116; (b) Uchida, T.; Saha, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 2521-2524.
29. For preliminary communication, see: (a) Saha, B.; Uchida, T.; Katsuki, T. Synlett 2001, 114-116; (b) Uchida, T.; Saha, B.; Katsuki, T. Tetrahedron Lett. 2001, 42, 2521-2524.
30. For preliminary communication, see: Saha B., Uchida T., Katsuki T. Chem. Lett. 2002;846-847.
31. Fukuda T., Katsuki T. Synlett. 1995;825-826
32. Idem, Tetrahedron 1997, 53, 7201-7208.
33. Lorkovic I.M., Miranda K.M., Lee B., Bernhard S., Schoonover J.R., Ford P.C. J. Am. Chem. Soc. 120:1998;11674-11683.
34. Takeda T., Irie R., Katsuki T. Synlett. 1999;1166-1168.
35. Doyle M.P., Winchester W.R., Hoorn J.A.A., Lynch V., Simonsen S.H. J. Am. Chem. Soc. 115:1993;9968-9978.
36. Davies H.M.L., Bruzinski P.R., Lake D.H., Kong N., Fall M.J. J. Am. Chem. Soc. 118:1996;6897-6907.
37. Maxwell J.L., O'Malley S., Brown K.C., Kodadek T. Organometallics. 11:1992;645-652.
38. Doyle M.P., Zhou Q.-L., Raab C.E., Roos G.H.P., Simonsen S.H., Lynch V. Inorg. Chem. 35:1996;6064-6073.
39. Doyle M.P., Kalinin A.V. J. Org. Chem. 61:1996;2179-2184.
40. Addition of N-methylimidazole has been reported to accelerate the reaction rate of Co-catalyzed cyclopropanation and to enhance its stereoselectivity. (a) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719-720; (b) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345-1346.
41. Addition of N-methylimidazole has been reported to accelerate the reaction rate of Co-catalyzed cyclopropanation and to enhance its stereoselectivity. (a) Yamada, T.; Ikeno, T.; Sekino, H.; Sato, M. Chem. Lett. 1999, 719-720; (b) Ikeno, T.; Sato, M.; Yamada, T. Chem. Lett. 1999, 1345-1346.
42. Enantioselectivity of intermolecular cyclopropanation catalyzed by complex 3 was also improved by the addition of N-methylimidazole (Ref. 3a).
43. Daniewski A.R., Wojceichowska W. J. Org. Chem. 47:1982;2993-2995.
44. Anderson K., Kuruvilla A., Uretsky N., Miller D. J. Med. Chem. 24:1981;683-687.
45. Jung M.E., Angelica S., D'Amico D.C. J. Org. Chem. 62:1997;9182-9187.
46. Fawzi M.M., Gutsche C.D. J. Org. Chem. 47:1966;1390-1393.
47. Julia S., Linstrumelle G. Bull. Soc. Chim. Fr. 11:1966;3490-3498.
48. Mori K., Matsui M. Tetrahedron. 25:1969;5013-5018.
49. Allen A.D., Fenwick M.F., Henry-Riad H., Tidwell T.T. J. Org. Chem. 66:2001;5759-5765.
50. Kim G.-S., Cho W.-C., Ahn H.K. Tetrahedron. 55:1999;10079-10086.
51. Chapman O.L., Rettig T.A., Griswold A.A., Dutton A.I., Fitton P. Tetrahedron Lett. 4:1963;2049-2055.
52. Cruciani G., Margeretha P. Helv. Chem. Acta. 73:1990;890-895.
53. Mash E.A., Nelson K.A. Tetrahedron. 43:1987;679-692.
54. Mash E.A., Torok D.S. J. Org. Chem. 54:1989;250-253.