Diastereoselective synthesis of strained spiro-cyclopropanooxindoles from cyclic diazoamides

Tetrahedron Letters

Volumn 51, Issue 43, 2010, Pages 5662-5665

  Muthusamy, Sengodagounder ^a   Azhagan, Datshanamoorthy ^a   Gnanaprakasam, Boopathy ^a   Suresh, Eringathodi ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

Author keywords

Copper(I) triflate; Cyclopropanation; Diazoamides; Oxindoles; Rhodium(II) acetate

Indexed keywords

ACETATE RHODIUM; ALKENE; AMIDE; COPPER COMPLEX; CYCLOPROPANOOXINDOLE DERIVATIVE; DIAZOAMIDE DERIVATIVE; INDOLE DERIVATIVE; RHODIUM COMPLEX; TRIFLUOROMETHANESULFONATE COPPER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLOPROPANATION; DIASTEREOISOMER; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 77957156901     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.159     Document Type: Article

References (42)

1. D.W. Robertson, J.H. Krushinski, G.D. Pollock, H. Wilson, R.F. Kauffman, and J.S. Hayes J. Med. Chem. 30 1987 824
2. Cordon, M. E.; Karp, G. M.; Birk, J. H. European Patent 459,133, 1991;
3. Chem. Abstr. 1992, 117, 48332
4. Condon, M. E.; Karp, G. M. European Patent 549,892, 1993;
5. Chem. Abstr. 1993, 119, 225817.
6. P.B. Alper, C. Meyers, A. Lerchner, D.R. Siegel, and E.M. Carreira Angew. Chem., Int. Ed. 38 1999 3186
7. C.B. Cui, H. Kakeya, G. Okada, R. Onose, M. Ubukata, I. Takahashi, K. Isono, and H. Osada J. Antibiot. 48 1995 1382
8. C.B. Cui, H. Kakeya, and H. Osada Tetrahedron 52 1996 12651
9. K.C. Chan, F. Morsingh, and G.B. Yeoh J. Chem. Soc. C: Org. 1966 2245
10. P.R. Sebahar, and R.M. Williams J. Am. Chem. Soc. 122 2000 5666
11. M.P. Doyle, M.A. McKervey, and T. Ye Modern Catalytic Methods for Organic Syntheis with Diazo Compounds. From Cyclopropanes to Ylides 1998 Wiley-Interscience New York
12. H.M.L. Davies B.M. Trost, I. Fleming, Comprehensive Organic Chemistry Vol. 4 1991 Pergamon Press New York 1031 1067
13. H.M.L. Davies, and E.G. Antoulinakis Organic Reactions 2001 John Wiley and Sons New York
14. M.P. Doyle Chem. Rev. 86 1986 919
15. T. Ye, and M.A. McKervey Chem. Rev. 94 1994 1091
16. H.-U. Reissig, and R. Zimmer Chem. Rev. 103 2003 1151
17. M.P. Doyle, and D.C. Forbes Chem. Rev. 98 1998 911 and references cited therein
18. J.A. Miller, W. Jin, and S.T. Nguyen Angew. Chem., Int. Ed. 41 2002 2953
19. H.M.L. Davies, and R.J. Townsend J. Org. Chem. 66 2001 6595
20. H.M.L. Davies, and S.A. Panaro Tetrahedron 56 2000 4781
21. M.P. Doyle, S.B. Davies, and W. Hu J. Chem. Soc., Chem. Commun. 2000 867
22. M.C. Pirrung, and Y.R. Lee J. Am. Chem. Soc. 117 1995 4814
23. M.C. Pirrung, and Y.R. Lee J. Chem. Soc., Chem. Commun. 1995 673
24. M.C. Pirrung, K. Lackey, J. Zhang, D.D. Sternbach, and F. Brown J. Org. Chem. 60 1995 2112
25. M.C. Pirrung, J. Zhang, and A.T. McPhail J. Org. Chem. 56 1991 6269
26. M.C. Pirrung, and F. Blume J. Org. Chem. 64 1999 3642
27. S. Muthusamy, S.A. Babu, C. Gunanathan, B. Ganguly, E. Suresh, and P. Dastidar J. Org. Chem. 67 2002 8019
28. S. Muthusamy, S.A. Babu, C. Gunanathan, E. Suresh, and P. Dastidar Bull. Chem. Soc. Jpn. 75 2002 801
29. S. Muthusamy, J. Krishnamurthi, S.A. Babu, and E. Suresh J. Org. Chem. 72 2007 1252
30. S. Muthusamy, J. Krishnamurthi, and M. Nethaji Chem. Commun. 2005 3862
31. S. Muthusamy, and B. Gnanaprakasam Tetrahedron 63 2007 3355
32. S. Muthusamy, C. Gunanathan, S.A. Babu, E. Suresh, and P. Dastidar J. Chem. Soc., Chem. Commun. 2002 824
33. S. Muthusamy, and C. Gunanathan Synlett 2002 1783
34. S. Muthusamy, and P. Srinivasan Tetrahedron Lett. 46 2005 1063
35. S. Muthusamy, and P. Srinivasan Tetrahedron Lett. 50 2009 3794
36. S. Muthusamy, B. Gnanaprakasam, and E. Suresh Org. Lett. 7 2005 4577
37. E.A. Lund, I.A. Kennedy, and A.G. Fallis Tetrahedron Lett. 34 1993 6841
38. A. Padwa, S.J. Coats, and L. Hadjiarapoglou Heterocycles 41 1995 1631
39. S. Muthusamy, and C. Gunanathan Synlett 2003 1559
40. General procedure for the synthesis of spiro-cyclopropanooxindoles 2-4, 8 and 9: To an oven-dried flask, a solution containing cyclic diazoamide 1 (1 mmol) and cyclic olefin (1.1 mmol) in dry dichloromethane (50 mL) under inert atmosphere was added 20 mol % of CuOTf or 2.0 mol % of rhodium(II) acetate dimer and stirred for appropriate duration at room temperature. The reaction was monitored by TLC and IR. After the decomposition of all diazoamide, the reaction mixture was evaporated and subjected to 100-200 mesh silica-gel column chromatography (EtOAc/hexane) to afford the respective spiro- cyclopropanooxindoles 2-4, 8 and 9.
41. +: 378.0929, found 378.0921.
42. Crystallographic data for 2d have been deposited (CCDC 647633) with the Cambridge Crystallographic Data Centre. Copy of the data can be obtained free of charge on application to 12, Union Road, Cambridge CB21EZ, UK (fax: +44 1223 336 033; e-mail: deposit@ccdc.cam.ac.uk ).