Reactions of cyclic diazoamides: Convenient synthesis of dispirocyclic cyclopropane systems

Synlett

Volumn , Issue 11, 2003, Pages 1599-1602

  Muthusamy, Sengodagounder ^a   Gunanathan, Chidambaram ^a  

^a CSIR CENTRAL SALT AND MARINE CHEMICALS RESEARCH INSTITUTE   (India)

Author keywords

Carbenoids; Diazo compounds; Indoles; Rhodium; Spiro compounds

Indexed keywords

ALKENE DERIVATIVE; AMIDE; CYCLOPROPANE DERIVATIVE; DIAZONIUM COMPOUND;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; CYCLOADDITION; CYCLOPROPANATION; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; X RAY ANALYSIS;

EID: 0042412074     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40996     Document Type: Article

References (44)

1. de Meijere, A. Chem. Rev. 2003, 103, 931.
2. (a) Small Ring Compounds in Organic Synthesis VI, Vol. 207; de Meijere, A., Ed.; Springer: Berlin, 2000.
3. (b) Methods of Organic Chemistry (Houben-Weyl), Vol. E 17c; de Meijere, A., Ed.; Thieme: Stuttgart, 1997.
4. (a) Lin, H.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2003, 42, 36.
5. (b) Ng, F. W.; Lin, H.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 9812.
6. (c) Overman, L. E.; Rosen, M. D. Angew. Chem. Int. Ed. 2000, 39, 4596.
7. (d) Nussbaum, F. V.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2000, 39, 2175.
8. (e) Sebahar, P. R.; Williams, R. M. J. Am. Chem. Soc. 2000, 122, 5666.
9. (a) Hegedus, L. S. Transition Metals in the Synthesis of Complex Organic Molecules; University Science Books: California, 1994.
10. (b) Ho, T. L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992.
11. Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. From Cyclopropanes to Ylides; Wiley-Interscience: New York, 1998.
12. For recent reviews see: (a) Mehta, G.; Muthusamy, S. Tetrahedron 2002, 58, 9477. (b) Doyle, M. P.; McKervey, M. A. Chem. Commun. 1997, 983. (c) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (d) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811.
13. For recent reviews see: (a) Mehta, G.; Muthusamy, S. Tetrahedron 2002, 58, 9477. (b) Doyle, M. P.; McKervey, M. A. Chem. Commun. 1997, 983. (c) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (d) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811.
14. For recent reviews see: (a) Mehta, G.; Muthusamy, S. Tetrahedron 2002, 58, 9477. (b) Doyle, M. P.; McKervey, M. A. Chem. Commun. 1997, 983. (c) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (d) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811.
15. For recent reviews see: (a) Mehta, G.; Muthusamy, S. Tetrahedron 2002, 58, 9477. (b) Doyle, M. P.; McKervey, M. A. Chem. Commun. 1997, 983. (c) Padwa, A.; Weingarten, M. D. Chem. Rev. 1996, 96, 223. (d) Miller, D. J.; Moody, C. J. Tetrahedron 1995, 51, 10811.
16. (a) Davies, H. M. L. In Comprehensive Organic Chemistry, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991, 1031-1067.
17. (b) Doyle, M. P. Chem. Rev. 1986, 86, 919.
18. (c) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091.
19. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
20. (a) Doyle, M. P.; Forbes, D. C. Chem. Rev. 1998, 98, 911; and references cited therein.
21. (b) Miller, J. A.; Jin, W.; Nguyen, S. T. Angew. Chem. Int. Ed. 2002, 41, 2953.
22. (c) Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595.
23. (d) Davies, H. M. L.; Panaro, S. A. Tetrahedron 2000, 56, 4781.
24. (e) Doyle, M. P.; Davies, S. B.; Hu, W. Chem. Commun. 2000, 867.
25. For cyclopropanation with diazoacetamides, see: Doyle, M. P.; Loh, K.-L. ; DeVries, K. M.; Chinn, M. S. Tetrahedron Lett. 1987, 28, 833.
26. (a) Pirrung, M. C.; Lee, Y. R. J. Am. Chem. Soc. 1995, 117, 4814.
27. (b) Pirrung, M. C.; Lee, Y. R. Chem. Commun. 1995, 673.
28. (c) Pirrung, M. C.; Lackey, K.; Zhang, J.; Sternbach, D. D.; Brown, F. J. Org. Chem. 1995, 60, 2112.
29. (d) Pirrung, M. C.; Zhang, J.; McPhail, A. T. J. Org. Chem. 1991, 56, 6269.
30. Pirrung, M. C.; Blume, F. J. Org. Chem. 1999, 64, 3642.
31. (a) Muthusamy, S.; Gunanathan, C.; Babu, S. A.; Suresh, E.; Dastidar, P. Chem. Commun. 2002, 824.
32. (b) Muthusamy, S.; Gunanathan, C. Syntett 2002, 1783.
33. (a) Muthusamy, S.; Gunanathan, C. Chem. Commun. 2003, 440.
34. (b) Muthusamy, S.; Babu, S. A.; Gunanathan, C.; Ganguly, B.; Suresh, E.; Dastidar, P. J. Org. Chem. 2002, 67, 8019.
35. (c) Muthusamy, S.; Gunanathan, C.; Babu, S. A. Synlett 2002, 787.
36. (d) Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2002, 43, 3931.
37. (e) Muthusamy, S.; Babu, S. A.; Gunanathan, C. Tetrahedron Lett. 2002, 43, 5981.
38. The structure of compounds 3d and 5b were unequivocally corroborated by single crystal X-ray analyses and will be disclosed in due course.
39. 2 using SHELXL-97 software.
40. Crystallographic data for 6a has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no CCDC-202639. Copies of the data can be obtained free of charge on application to 12, Union Road, Cambridge CB2 1EZ, UK. (Fax: +44.(1223)336033; e-mail: deposit@ccdc.cam.ac.uk).
41. Dowd, P.; Kaufman, C.; Paik, Y. H. Tetrahedron Lett. 1985, 26, 2283.
42. The possibility of formation of olefins 7 from the cyclopropane 6 by ring opening under the experimental condition is ruled out by performing the control experiments by reapplying the reaction conditions on the isolated pure products 6.
43. Müller, P.; Tohil, S. Tetrahedron 2000, 56, 1725.
44. Similar trend was also observed in our earlier studies of C-H insertion reactions using these cyclic diazo carbonyl compounds. See ref. 13.