Enantioselective desymmetrization of prochiral 1,3-dinitropropanes via organocatalytic allylic alkylation

Chemical Communications

Volumn 50, Issue 1, 2014, Pages 121-123

  Jyoti Singha Roy, Soumya ^a   Mukherjee, Santanu ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 DINITROPROPANE; PROPANE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; DIASTEREOISOMER; ENANTIOSELECTIVE DESYMMETRIZATION; ENANTIOSELECTIVITY; ORGANOCATALYTIC ALLYLIC ALKYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 84888580185     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc47645f     Document Type: Article

References (37)

1. H. M. L. Davies, E. J. Sorensen, Chem. Soc. Rev., 2009, 38, 2981
2. E. García-Urdiales, I. Alfonso, V. Gotor, Chem. Rev., 2011, 111, PR110
3. T. Rovis, in New Frontiers in Asymmetric Catalysis, ed. K. Mikami and M. Lautens, Wiley, Hoboken, NJ, 2007, p. 275
4. M. C. Willis, J. Chem. Soc., Perkin Trans. 1, 1999, 1765
5. L. S. Aitken, N. R. Arezki, A. Dell'Isola, A. J. A. Cobb, Synthesis, 2013, 2627
6. N. Ono, in The Nitro Group in Organic Synthesis, Wiley-VCH, Weinheim, 2001
7. R. Ballini, G. Bosica, D. Fiorini, A. Palmieri, Synthesis, 2004, 1938
8. L. Barboni, S. Gabrielli, A. Palmieri, C. Femoni, R. Ballini, Chem. Eur. J., 2009, 15, 7867
9. D. Y. Park, K. Y. Lee, S. Gowrisankar, J. N. Kim, Bull. Korean Chem. Soc., 2008, 29, 701
10. D. Y. Park, K. Y. Lee, J. N. Kim, Tetrahedron Lett., 2007, 48, 1633
11. R. Ballini, L. Barboni, D. Fiorini, G. Giarlo, A. Palmieri, Chem. Commun., 2005, 2633
12. E. Reyes, H. Jiang, A. Milelli, P. Elsner, R. G. Hazell, K. A. Jørgensen, Angew. Chem., Int. Ed., 2007, 46, 9202
13. B. M. Trost, J.-P. Surivet, Angew. Chem., Int. Ed., 2000, 39, 3122
14. B. M. Trost, M. L. Crawley, Chem. Rev., 2003, 103, 2921
15. X.-F. Yang, W.-H. Yu, C.-H. Ding, Q.-P. Ding, S.-L. Wan, X.-L. Hou, L.-X. Dai, P.-J. Wang, J. Org. Chem., 2013, 78, 6503
16. X.-F. Yang, C.-H. Ding, X.-H. Li, J.-Q. Huang, X.-L. Hou, L.-X. Dai, P.-J. Wang, J. Org. Chem., 2012, 77, 8980
17. G.-Y. Chen, F. Zhong, Y. Lu, Org. Lett., 2012, 14, 3955
18. G.-Y. Chen, F. Zhong, Y. Lu, Org. Lett., 2011, 13, 6070
19. D. Basavaiah, J. S. Rao, Tetrahedron Lett., 2004, 45, 1621
20. J. M. Kim, Y. J. Im, T. H. Kim, J. N. Kim, Bull. Korean Chem. Soc., 2002, 23, 657
21. S. W. Smith, G. C. Fu, J. Am. Chem. Soc., 2009, 131, 14231
22. D. Basavaiah, B. S. Reddy, S. S. Badsara, Chem. Rev., 2010, 110, 5447
23. X. Companyó, A. Mazzanti, A. Moyano, A. Janecka, R. Rios, Chem. Commun., 2013, 49, 1184
24. F. Zhong, J. Luo, G.-Y. Chen, X. Dou, Y. Lu, J. Am. Chem. Soc., 2012, 134, 10222
25. T. Furukawa, J. Kawazoe, W. Zhang, T. Nishimine, E. Tokunaga, T. Matsumoto, M. Shiro, N. Shibata, Angew. Chem., Int. Ed., 2011, 50, 9684
26. H.-L. Cui, J.-R. Huang, J. Lei, Z.-F. Wang, S. Chen, L. Wu, Y.-C. Chen, Org. Lett., 2010, 12, 720
27. Q.-L. Wang, L. Peng, F.-Y. Wang, M.-L. Zhang, L.-N. Jia, F. Tian, X.-Y. Xu, L.-X. Wang, Chem. Commun., 2013, 49, 9422
28. F. Zhong, G.-Y. Chen, X. Han, W. Yao, Y. Lu, Org. Lett., 2012, 14, 3764
29. F. Zhong, X. Han, Y. Wang, Y. Lu, Angew. Chem., Int. Ed., 2011, 50, 7837
30. T.-Y. Liu, M. Xie, Y.-C. Chen, Chem. Soc. Rev., 2012, 41, 4101
31. L.-Q. Lu, X.-L. An, J.-R. Chen, W.-J. Xiao, Synlett, 2012, 490
32. J. Alemán, A. Parra, H. Jiang, K. A. Jørgensen, Chem. Eur. J., 2011, 17, 6890
33. W.-Y. Siau, J. Wang, Catal. Sci. Technol., 2011, 1, 1298
34. Y. Takemoto, Chem. Pharm. Bull., 2010, 58, 593
35. S. J. Connon, Chem. Commun., 2008, 2499
36. T. Okino, Y. Hoashi, Y. Takemoto, J. Am. Chem. Soc., 2003, 125, 12672
37. H.-L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, Y.-C. Chen, Angew. Chem., Int. Ed., 2009, 48, 5737