A novel [3+2] dipolar cycloaddition approach to hexahydrobenzofuro [3,2-b] pyrroles

Synlett

Volumn , Issue 13, 2008, Pages 2069-2071

  Kim, Ikyon ^a   Na, Hee Kyung ^a   Kim, Kyung Ran ^a   Kim, Sun Gi ^a   Lee, Ge Hyeong ^a  

^a Korea Research Institute of Chemical Technology   (South Korea)

Author keywords

1,3 Dipolar cycloadditions; 2 Vinyloxybenzaldehydes; Azomethine ylides; Hexahydrobenzofuro 3,2 b pyrroles; Intramolecular reaction; Stereoselective synthesis

Indexed keywords

HEXAHYDROBENZOFURO[3,2 B]PYRROLE DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 49649108896     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1077951     Document Type: Article

References (18)

1. Kim, I.; Kim, S. G.; Choi, J.; Lee, G. H. Tetrahedron 2008, 64, 664.
2. For chapters and reviews on 1,3-dipolar cycloadditions, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1990, Chap. 6, 269.
3. (b) Padwa, A. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991, 1069.
4. (c) Wade, P. A. In Comprehensive Organic Synthesis, Vol. 4; Trost, B. M.; Fleming, I., Eds.; Pergamon Press: New York, 1991, 1111.
5. (d) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products; Padwa, A.; Pearson, W., Eds.; Wiley and Sons: New York, 2003.
6. (e) Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.
7. (f) Nair, V.; Suja, T. D. Tetrahedron 2007, 63, 12247.
8. +: 305.1263; found: 305.1265.
9. CCDC 683322 contains the supplementary crystallographic data for compound 7a. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
10. 1,3-Dipolar cycloaddition reactions of azomethine ylides derived from 2-allyloxybenzaldehydes or 2-propargyloxybenzaldehydes are well studied as compared to our present work. For selected examples, see: (a) Pospíšil, J.; Potáček, M. Tetrahedron 2007, 63, 337.
11. (b) Zhang, W.; Lu, Y.; Geib, S. Org. Lett. 2005, 7, 2269.
12. (c) Bashiardes, G.; Safir, I.; Barbot, F.; Laduranty, J. Tetrahedron Lett. 2004, 45, 1567.
13. (d) Bashiardes, G.; Safir, I.; Mohamad, A. S.; Barbot, F.; Laduranty, J. Org. Lett. 2003, 5, 4915.
14. (e) Grigg, R.; Duffy, L. M.; Dorriry, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213.
15. (f) Amornraksa, K.; Barr, D.; Donegan, G.; Grigg, R.; Ratananukul, P.; Sridharan, V. Tetrahedron 1989, 45, 4649.
16. (g) Kanemasa, S.; Sakamoto, K.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 1960.
17. For a [3+2] cycloaddition of azomethine ylides derived from 2-allylbenzaldehyde, see: Carroll, F. I.; Blough, B. E.; Mascarella, S. W.; Xu, H.; Goodman, C. B.; Rothman, R. B. Med. Chem. Res. 1993, 3, 178.
18. Yields were not optimized.