Chemo- and diastereoselective synthesis of spiro-dioxolanes from intermolecular carbonyl ylide cycloaddition with aryl aldehyde

Tetrahedron Letters

Volumn 52, Issue 1, 2011, Pages 148-150

  Muthusamy, Sengodagounder ^a   Ramkumar, Rajagopal ^a   Mishra, Ananta Kumar ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

Author keywords

Carbenoids; Carbonyl ylides; Diazoamides; Dioxolanes; Oxindoles; Rhodium(II) acetate

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; ALDEHYDE DERIVATIVE; CARBONYL DERIVATIVE;

ARTICLE; CATALYST; CYCLOADDITION; DIASTEREOISOMER; ELECTRON TRANSPORT; ROOM TEMPERATURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 78649837750     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.005     Document Type: Article

References (36)

1. M.P. Doyle, M.A. McKervey, and T. Ye Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. From Cyclopropanes to Ylides 1998 Wiley-Interscience New York
2. A. Padwa, W.H. Pearson, Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products 2003 John Wiley & Sons New Jersey
3. A. Padwa, and S. Hornbuckle Chem. Rev. 91 1991 263 309
4. A. Padwa, and M.D. Weingarten Chem. Rev. 96 1996 223 269
5. G. Mehta, and S. Muthusamy Tetrahedron 58 2002 9477 9504
6. A. Padwa J. Organomet. Chem. 690 2005 5533 5540
7. S. Muthusamy, and J. Krishnamurthi Top. Hetereocycl. Chem. 12 2008 147 192
8. M.P. Doyle, W. Hu, and D.J. Timmons Org. Lett. 3 2001 933 935
9. H.M.L. Davies, and J. DeMeese Tetrahedron Lett. 42 2001 6803 6805
10. S. Muthusamy, C. Gunanathan, and M. Nethaji Synlett 2004 639 642
11. S. Torssella, and P. Somfaia Adv. Synth. Catal. 348 2006 2421 2430
12. A.E. Russell, J. Brekan, L. Gronenberg, and M.P. Doyle J. Org. Chem. 69 2004 5269 5274
13. S. Muthusamy, C. Gunanathan, and M. Nethaji J. Org. Chem. 69 2004 5631 5637
14. V. Nair, S. Mathai, and R. Luxmi Varma J. Org. Chem. 69 2004 1413 1414
15. R. Huisgen, and P. de March J. Am. Chem. Soc. 104 1982 4953 4954
16. S. Torssella, P. Somfaia, and M. Kienle Angew. Chem., Int. Engl. 44 2005 3096 3099
17. M. Hamaguchi, N. Tomida, and Y. Iyama J. Org. Chem. 72 2007 1326 1334
18. R.P. L'Esperance, T.M. Ford, and M. Jones Jr. J. Am. Chem. Soc. 110 1988 209 213
19. M.-Z. Wang, H.-W. Xu, Y. Liu, M.-K. Wong, and C.-M. Che Adv. Synth. Catal. 348 2006 2391 2396
20. P. de March, and R. Huisgen J. Am. Chem. Soc. 104 1982 4952
21. M.P. Doyle, D.C. Forbes, M.N. Protopopova, S.A. Stanley, M.M. Vasbinder, and K.R. Xavier J. Org. Chem. 62 1997 7210 7215
22. C.-D. Lu, Z.-Y. Chen, H. Liu, W.-H. Hu, and A.-Q. Mi Org. Lett. 6 2004 3071
23. A.D. Angelis, P. Panne, G.P.A. Yap, and J.M. Fox J. Org. Chem 73 2008 1435 1439
24. V. Nair, S. Mathai, S.M. Nair, and N.P. Rath Tetrahedron Lett. 44 2003 8407 8409
25. V. Nair, S. Mathai, S.M. Nair, C. Mathew, and N.P. Rath Tetrahedron 61 2005 2849 2856
26. B. Jiang, X.-B. Zhang, and Z.-H. Luo Org. Lett. 4 2002 2453 2455
27. S. Muthusamy, and B. Gnanaprakasam Tetrahedron 63 2007 3355 3362
28. S. Muthusamy, J. Krishnamurthi, S.A. Babu, and E. Suresh J. Org. Chem. 72 2007 1252 1262
29. S. Muthusamy, B. Gnanaprakasam, and E. Suresh Org. Lett. 7 2005 4577 4580
30. S. Muthusamy, J. Krishnamurthi, and M. Nethaji Chem. Commun. 2005 3862 3864
31. S. Muthusamy, J. Krishnamurthi, and E. Suresh Synlett 2005 3002 3004
32. S. Muthusamy, S.A. Babu, C. Gunanathan, B. Ganguly, E. Suresh, and P. Dastidar J. Org. Chem. 67 2002 8019 8033
33. +: 531.1532, found 531.1521.
34. Crystallographic data for 4a have been deposited (CCDC 782974) 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 ).
35. +: 531.1532, found 531.1539.
36. +: 501.1426, found 501.1438.