The high pressure reaction of cyclopropanes with indoles catalyzed by ytterbium triflate

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 5949-5952

  Harrington, Paul ^a   Kerr, Michael A ^a  

^a ACADIA UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; IN VITRO STUDY; PRESSURE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030788247     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01351-8     Document Type: Article

References (12)

1. Harrington, P.E.; Kerr, M.A. Synlett 1996, 1047.
2. For a review see: Marshman, R.W. Aldrichimica Acta 1995, 28, 77
3. a) Black, W.C., Bayly, C.; Belley, M.; Chan, C.-C.; Charleson, S.; Denis, D.; Gauthier, J.Y.; Gordon, R.; Quay, D.; Kargman, S.; Lau, C.K.; Leblanc, Y.; Mancini, J.; Quellet, M.; Percival, D.; Roy, P.; Skorey, K.; Tagari, P.; Vickers, P.; Wong, E.; Xu, L.; Prasit, P. Bioorg. Med. Chem. Lett. 1996, 725.
4. b) Leblanc, Y.; Black, W.C., Chan, C.-C.; Charleson, Delorme, D.; Denis, D.; Gauthier, J.Y.; Grimm, E.L.; Gordon, R.; Guay, D.; Hamel, P.; Kargman, S.; Lau, C.K.; Mancini, J.; Quellet, M.; Percival, D.; Roy, P.; Skorey, K.; Tagari, P.; Vickers, P.; Wong, E.; Xu, L.; Prasit, P. Bioorg. Med. Chem. Lett. 1996, 731.
5. General procedure: The indole and the cyclopropane (about 1 mmol of limiting reagent) were measured into a length of heat shrinkable Teflon tubing closed at one end with a brass clamp. The solvent (1 mL/mmol of limiting reagent) was added followed by the catalyst. The tube was sealed with another brass clamp and placed in a LECO Tempres high-pressure chemical reactor and the reactor pressurized. After a period of time the mixture was depressurized and the solvent removed. The residue was subjected to flash chromatography on silica gel and the product isolated as a pure oil.
6. Jenner, G. Tetrahedron Lett. 1995, 233.
7. a) Chen, D.; Yu, L.; Wang, P.G. Tetrahedron Lett. 1996, 4467.
8. b) Yu, L.; Chen, D.; Wang, P.G. Tetrahedron Lett. 1996, 2169.
9. c) Kobayashi, S. Synlett, 1994, 689.
10. a) Magnus, P.; Schultz, J.; Gallagher, T. J. Am. Chem. Soc. 1985, 707, 1984.
11. b) Corey, E.J.; Chaykovsky, M. J. Am. Chem. Soc. 1965, 87, 1965.
12. 13C NMR, IR, and mass spectra.