Thermodynamic control of diastereoselectivity in the formal nucleophilic substitution of bromocyclopropanes

Organic Letters

Volumn 12, Issue 7, 2010, Pages 1488-1491

  Banning, Joseph E ^a   Prosser, Anthony R ^a   Rubin, Michael ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; CYCLOPROPANOL; ETHER DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS; THERMODYNAMICS;

CYCLOPROPANES; ETHERS; ETHERS, CYCLIC; MOLECULAR STRUCTURE; STEREOISOMERISM; THERMODYNAMICS;

EID: 77950243266     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100187c     Document Type: Article

References (24)

1. For reviews, see: (a) Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
2. (b) Rubin, M.; Rubina, M.; Gevorgyan, V. Synthesis 2006, 1221.
3. (c) Marek, I.; Simaan, S.; Masarwa, A. Angew. Chem., Int. Ed. 2007, 46, 7364.
4. (d) Fox, J. M.; Yan, N. Curr. Org. Chem. 2005, 9, 719.
5. For recent contributions, see: (a) Tarwade, V.; Liu, X.; Yan, N.; Fox, J. M. J. Am. Chem. Soc. 2009, 131, 5382.
6. (b) Sherrill, W. M.; Rubin, M. J. Am. Chem. Soc. 2008, 130, 13804.
7. (c) Alnasleh, B. K.; Sherrill, W. M.; Rubin, M. Org. Lett. 2008, 10, 3231.
8. (d) Levin, A.; Marek, I. Chem. Commun. 2008, 4300.
9. (e) Yan, N.; Liu, X.; Fox, J. M. J. Org. Chem. 2008, 73, 563.
10. (f) Trofimov, A.; Rubina, M.; Rubin, M.; Gevorgyan, V. J. Org. Chem. 2007, 72, 8910.
11. (g) Simaan, S.; Marek, I. Org. Lett. 2007, 9, 2569.
12. Alnasleh, B. K.; Sherrill, W. M.; Rubina, M.; Banning, J.; Rubin, M. J. Am. Chem. Soc. 2009, 131, 6906.
13. For preparative synthesis of cyclopropenes via this route, see: Sherrill, W. M.; Kim, R.; Rubin, M. Synthesis 2009, 1477.
14. There is a single precedent of formal substitution (Nu ) MeO) of 2-bromocyclopropanecarboxylic acid derivative, which provided marginal yield and poor diastereoselectivity. See: Taylor, E. C.; Hu, B. Synth. Commun. 1996, 26, 1041.
15. For trans-selective formal nucleophilic substitution of 2-bromocyclopropanecarboxylate with tert-butoxide, see: Wiberg, K. B.; Barnes, R. K.; Albin, J. J. Am. Chem. Soc. 1957, 79, 4994.
16. Starting 2-bromocyclopropanecarboxamides are readily available from the known 2,2-dibromocyclopropanecarbonyl chloride via reaction with the corresponding amine, followed by partial reduction of halogen with i-PrMgBr. See Supporting Information for details.
17. For direct transition metal-catalyzed addition of terminal alkynes across the double bond of cyclopropenes, see: Yin, J.; Chisholm, J. D. Chem. Commun. 2006, 632.
18. 5Br, see: (a) Chandru, H.; Sharada, A. C.; Bettadaiah, B. K.; Ananda, K., C. S.; Rangappa, K. S.; Jayashree, K. Bioorg. Med. Chem. 2007, 15, 7696.
19. (b) Corbett, J. W.; Rauckhorst, M. R.; Qian, F.; Hoffman, R. L.; Knauer, C. S.; Fitzgerald, L. W. Bioorg. Med. Chem. Lett. 2007, 17, 6250-6256.
20. (c) Chiu, G.; Li, S.; Connolly, P. J.; Pulito, V.; Liu, J.; Middleton, S. A. Bioorg. Med. Chem. Lett. 2007, 17, 3930.
21. (d) van Tilburg, E. W.; van der Klein, P. A. M.; von Frijtag Drabbe Kuenzel, J. K.; de Groote, M.; Stannek, C.; Lorenzen, A.; Ijzerman, A. P. J. Med. Chem. 2001, 44, 2966.
22. σ(-)-Values used are derived from Swain-Lupton parameters adopted from: (a) Swain, C. G.; Lupton, E. C., Jr. J. Am. Chem. Soc. 1968, 90, 4328.
23. (b) Williams, S. G.; Norrington, F. E. J. Am. Chem. Soc. 1976, 98, 508.
24. This was confirmed by the fact that the overall kinetic rate of the transformation did not depend on electronic properties of the phenoxide species