Highly enantioselective intramolecular cyclopropanation of alkenyl diazo ketones using Ru(salen) as catalyst

Chemistry Letters

Volumn , Issue 8, 2002, Pages 846-847

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

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

KETONE DERIVATIVE; RUTHENIUM DERIVATIVE;

ARTICLE; CATALYST; CHIRALITY; CONFORMATION; CYCLIZATION; CYCLOPROPANATION; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRRADIATION;

EID: 0037025493     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2002.846     Document Type: Article

References (28)

1. For a recent review, see: a) M. P. Doyle, "Catalytic Asymmetric Synthesis," ed. by I. Ojima, Wiley-VCH, New York (2000), Chap. 5, p 191.
2. b) A. Pfaltz, K. M. Lydon, A. M. McKervey, A. B. Charette, and H. Level, "Comprehensive Asymmetric Catalysis," ed. by E. N. Jacobsen, A. Pfaltz, and H. Yamamoto, Springer, Berlin (1999), Chap. 16.
3. M. P. Doyle and M. N. Protopopova, Tetrahedron, 54, 7919 (1998).
4. T. Niimi, T. Uchida, R. Irie, and T. Katsuki, Adv. Synth. Catal., 343, 79 (2001).
5. a) M. P. Doyle, C. S. Peterson, Q.-L. Zhou, and H. Nishiyama, J. Chem. Soc., Chem. Commun. 1997, 211.
6. b) M. P. Doyle, C. S. Peterson, and D. L. Parker, Jr., Angew. Chem., Int. Ed. Engl., 35, 1334 (1996).
7. M. P. Doyle, R. E. Austin, A. S. Bailey, M. P. Dwyer, A. B. Dyatkin, A. V. Kalinin, M. M. Y. Kwan, S. Liras, C. J. Oalmann, R. J. Pieters, M. N. Protopopova, C. E. Raab, G. H. Roos, Q.-L. Zhou, and S. F. Martin, J. Am. Chem. Soc., 117, 5763 (1995).
8. M. P. Doyle, A. B. Dyatkin, A. V. Kalinin, D. A. Rupper, S. F. Martin, M. R. Spallar, and S. Liras, J. Am. Chem. Soc., 117, 11021 (1995).
9. a) H. M. L. Davies and B. D. Doan, Tetrahedron Lett., 37, 3967 (1996).
10. b) H. M. L. Davies and B. D. Doan, J. Org. Chem., 64, 8501 (1999).
11. a) S.-B. Park, K. Murata, H. Matsumoto, and H. Nishiyama, Tetrahedron: Asymmetry, 6, 2487 (1995).
12. b) C.-M. Che, J.-S. Huang, F.-W. Lee, Y. Li, T.-S. Lai, H.-L. Kwong, P.-F. Teng, W.-S. Lee, W.-C. Lo, S.-M. Peng, and Z.-Y. Zhou, J. Am. Chem. Soc., 123, 4119 (2001).
13. c) B. Saha, T. Uchida, and T. Katsuki, Synlett, 2001, 114.
14. d) I. J. Munslow, K. M. Gillespie, R. J. Deeth, and P. Scott, Chem. Commun., 2001, 1638.
15. T. Uchida, B. Saha, and T. Katsuki, Tetrahedron Lett., 42, 2521 (2001).
16. C. Piqué, B. Fähndrich, and A. Pfaltz, Synlett, 1995, 491.
17. a) R. Tokunoh, H. Tomiyama, M. Sodeoka, and M. Shibasaki, Tetrahedron Lett., 37, 2449 (1996).
18. b) P. Müller and C. Boléa, Synlett, 2000, 826.
19. G.-S. Kim, W.-C. Cho, and H. K. Ahn, Tetrahedron, 55, 10079 (1999).
20. W.-S. Park, H.-J. Son, G.-S. Kim, and H. K. Ahn, Tetrahedron: Asymmetry, 10, 1903 (1999).
21. D.-J. Cho, S.-J. Jeon, H.-S. Kim, C.-S. Cho, S.-C. Shim, and T.-J. Kim, Tetrahedron: Asymmetry, 10, 3833 (1999).
22. M. P. Doyle, M. Y. Eismont, and Q. L. Zhou, Russ. Chem. Bull., 46, 955 (1997).
23. a) M. Barberis, J. Pérez-Prieto, S.-E. Stribia, and P. Lahuerta, Org. Lett, 3, 3317 (2001).
24. M. Barberis, J. Pérez-Prieto, K. Herbst, and P. Lahuerta, Organometallics, 21, 1667 (2002). Although the enantioselectivity of the cyclopropanation giving [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.
25. P. Müller and E. Maitreiean, Collect. Czech. Chem. Commun., 64, 1807 (1999).
26. T. Uchida, R. Irie, and T. Katsuki, Tetrahedron, 56, 3501 (2000).
27. T. Katsuki, Adv. Synth. Catal., 34, 131 (2002).
28. 2. To this mixture was added a THF solution (1 ml) of (E)-1-diazo-6-phenyl-5-hexen-2-one (20 mg, 0.1 mmol) dropwise over a period of 12 h using a syringe pump under irradiation of incandescent light. The reaction mixture was stirred for another 4 h and concentrated in vacuo. The residue was chromatographed on silica gel using hexane and ethyl acetate (11 : 1) as eluent to yield bicyclic ketone (13.5 mg) in 78% yield. The enantiomeric excess of the product was determined as described in the footnote a of Table 1.