Stereoselective synthesis of 1,2,2-trisubstituted indane derivatives using a tandem SN2-michael addition sequence

Synlett

Volumn , Issue 12, 2007, Pages 1889-1892

  Gharpure, Santosh J ^a   Reddy, S Raja Bhushan ^a   Sanyal, Udishnu ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

Alkylation reactions; Indane derivatives; Indanopiperidines; Michael additions; Tandem reactions

Indexed keywords

INDAN DERIVATIVE; INDANOPIPERIDINE DERIVATRIVE; SPIROINDANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CRYSTAL STRUCTURE; MICHAEL ADDITION; STEREOCHEMISTRY; SYNTHESIS;

EID: 34547638110     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984526     Document Type: Article

References (28)

1. For reviews of indane derivatives of biological interest, see: (a) Galatsis, P. Ann. Rep. Med. Chem. 1998, 33, 327.
2. (b) Ganellin, C. R. Adv. Drug Res. 1967, 4, 163.
3. For reviews on benzoannelated fenestranes and centropolyindanes, see: (a) Kuck, D. Chem. Rev. 2006, 106, 4885.
4. (b) Kuck, D. Advances in Theoretically Interesting Molecules, Vol. 4; Thummel, R. P., Ed.; JAI Press: Greenwich, London, 1998, 81-155.
5. (c) Kuck, D. Top. Curr. Chem. 1998, 196, 167; and references therein.
6. For some recent examples, see: (a) Davies, I. W.; Senanayake, C. H.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. Tetrahedron Lett. 1996, 37, 1725.
7. (b) Liang, G.; Trauner, D. J. Am. Chem. Soc. 2004, 126, 9544.
8. (c) Kurosu, M.; Porter, J. R.; Foley, M. A. Tetrahedron Lett. 2004, 45, 145.
9. For reviews on the synthesis of indane derivatives, see: (a) Hong, B.-C.; Sarshar, S. Org. Prep. Proced. Int. 1999, 31, 1.
10. (b) Ferraz, H. M. C.; Aguilar, A. M.; Silva, L. F. Jr.; Craveiro, M. V. Quim. Nova 2005, 28, 703.
11. (a) Bunce, R. A. Tetrahedron 1995, 51, 13103.
12. (b) Nicolaou, K. C.; Edmonds, D. J.; Bulger, P. G. Angew. Chem. Int. Ed. 2006, 45, 7134.
13. (c) Nicolaou, K. C.; Montagnon, T.; Snyder, S. A. Chem. Commun. 2003, 551.
14. For some selected examples of tandem alkylation-Michael reaction sequence for the synthesis of heterocycles and carbocycles, see: (a) Bunce, R. A.; Peeples, C. J.; Jones, P. B. J. Org. Chem. 1992, 57, 1727.
15. (b) Bunce, R. A.; Kotturi, S. V.; Peeples, C. J.; Holt, E. M. J. Heterocycl. Chem. 2002, 39, 1049.
16. (c) Bunce, R. A.; Allison, J. C. Synth. Commun. 1999, 29, 2175.
17. (d) Goff, D. A. Tetrahedron Lett. 1998, 39, 1473.
18. (e) Watanabe, H.; Onoda, T.; Kitahara, T. Tetrahedron Lett. 1999, 40, 2545.
19. (f) Le Dreau, M.-A.; Desmaele, D.; Dumas, F.; d'Angelo, J. J. Org. Chem. 1993, 58, 2933.
20. (g) Desmaele, D.; Louvet, J.-M. Tetrahedron Lett. 1994, 35, 2549.
21. (h) Srikrishna, A.; Reddy, T. J.; Kumar, P. P. Synlett 1997, 663.
22. (i) Prabhu, K. R.; Sivanand, P. S.; Chandrasekaran, S. Angew. Chem. Int. Ed. 2000, 39, 4316.
23. (j) Liu, H.-J.; Han, Y. J. Chem. Soc., Chem. Commun. 1991, 1484.
24. Lindsell, W. E.; Palmer, D. D.; Preston, P. N.; Rosair, G. M.; Jones, R. V. H.; Whitton, A. J. Organometallics 2005, 24, 1119.
25. 3: 256.1287; found: 260.1291.
26. 8 (118.0 mg, 81%) as a viscous oil.
27. 5S; unit cell parameters: a = 12.8473 (3), b = 9.1054 (2), c = 18.5010 (4) Å, a = 90.00°, β = 95.8910 (10)°, γ = 90.00°; space group P2 (1)/c; CCDC number 638872. CCDC 638873 and CCDC 638872 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
28. Meyer, M. D.; DeBernardis, J. F.; Hancock, A. A. J. Med. Chem. 1994, 37, 105.