Direct stereospecific synthesis of unprotected N-H and N-Me aziridines from olefins

Science

Volumn 343, Issue 6166, 2014, Pages 61-65

  Jat, Jawahar L ^a   Paudyal, Mahesh P ^a   Gao, Hongyin ^a   Xu, Qing Long ^a   Yousufuddin, Muhammed ^b   Devarajan, Deepa ^c   Ess, Daniel H ^c   K̈urti, Lászĺo ^a   Falck, John R ^a  

^a UNIVERSITY OF TEXAS SOUTHWESTERN MEDICAL CENTER   (United States)

^b UNIVERSITY OF TEXAS AT ARLINGTON   (United States)

^c Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; AZIRIDINE DERIVATIVE; RHODIUM; ALKENE; BIOLOGICAL PRODUCT; HYDROGEN; HYDROXYLAMINE; NITROGEN; O (2,4 DINITROPHENYL)HYDROXYLAMINE; O-(2,4-DINITROPHENYL)HYDROXYLAMINE;

CATALYSIS; ORGANIC COMPOUND; OXIDANT; PHENOLIC COMPOUND; QUANTUM MECHANICS; REACTION KINETICS; RHODIUM;

AMINATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; DECOMPOSITION; ELECTRON; ENVIRONMENTAL TEMPERATURE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; STEREOSPECIFICITY; SYNTHESIS; CATALYSIS; CHEMISTRY;

ALKENES; AZIRIDINES; BIOLOGICAL PRODUCTS; CATALYSIS; HYDROGEN; HYDROXYLAMINES; NITROGEN;

EID: 84892747265     PISSN: 00368075     EISSN: 10959203     Source Type: Journal    
DOI: 10.1126/science.1245727     Document Type: Article

References (41)

1. W. McCoull, F. A. Davis, Synthesis 2000, 1347-1365 (2000).
2. J. B. Sweeney, Chem. Soc. Rev. 31, 247-258 (2002).
3. C. Botuha, F. Chemla, F. Ferreira, A. Perez-Luna, in Heterocycles in Natural Product Synthesis, K. C. Majumdar, S. K. Chattopadhyay, Eds. (Wiley-VCH, Weinheim, Germany, 2011), pp. 3-39.
4. C. Ogawa, S. Kobayashi, in Science of Synthesis, Water in Organic Synthesis, S. Kobayashi, Ed. (Thieme, Stuttgart, 2012), pp. 579-599.
5. R. Chawla, A. K. Singh, L. D. S. Yadav, RSC Adv. 3, 11385-11403 (2013).
6. J. T. Njardarson, Synlett 24, 787-803 (2013).
7. P. A. S. Lowden, in Aziridines and Epoxides in Organic Synthesis, A. K. Yudin, Ed. (Wiley-VCH, Weinheim, Germany, 2006), pp. 399-442.
8. F. M. D. Ismail, D. O. Levitsky, V. M. Dembitsky, Eur. J. Med. Chem. 44, 3373-3387 (2009).
9. C. J. Thibodeaux, W. C. Chang, H. W. Liu, Chem. Rev. 112, 1681-1709 (2012).
10. H. M. I. Osborn, J. Sweeney, Tetrahedron Asymmetry 8, 1693-1715 (1997).
11. E. N. Jacobsen, in Comprehensive Asymmetric Catalysis, E. N. Jacobsen, A. Pfaltz, H. Yamamoto, Eds. (Springer, Berlin, 1999), vol. 2, pp. 607-618.
12. P. Müller, C. Fruit, Chem. Rev. 103, 2905-2920 (2003).
13. C. Moessner, C. Bolm, in Transition Metals for Organic Chemistry: Building Blocks and Fine Chemicals, M. Beller, C. Bolm, Eds. (Wiley-VCH, Weinheim, Germany, ed. 2, 2004), vol. 2, pp. 389-402.
14. V. K. Aggarwal, D. M. Badine, V. A. Moorthie, in Aziridines and Epoxides in Organic Synthesis, A. K. Yudin, Ed. (Wiley-VCH, Weinheim, Germany, 2006), pp. 1-35.
15. G. Cardillo, L. Gentilucci, A. Tolomelli, in Asymmetric Synthesis of Nitrogen Heterocycles, J. Royer, Ed. (Wiley-VCH, Weinheim, Germany, 2009), pp. 3-50.
16. J. Sweeney, Eur. J. Org. Chem. 2009, 4911-4919 (2009).
17. H. Pellissier, Tetrahedron 66, 1509-1555 (2010).
18. S. Ye, Y. Tang, in Handbook of Cyclization Reactions, S. Ma, Ed. (Wiley-VCH, Weinheim, Germany, 2010), vol. 2, pp. 687-732.
19. D. Karila, R. H. Dodd, Curr. Org. Chem. 15, 1507 (2011).
20. H. Muchalski, J. N. Johnston, in Science of Synthesis, Stereoselective Synthesis (Thieme, Stuttgart, 2011), vol. 1, pp. 155-184.
21. D. M. Jenkins, Synlett 23, 1267-1270 (2012).
22. H. Jiang, X. P. Zhang, in Comprehensive Chirality, E. M. Carreira, H. Yamamoto, Eds. (Elsevier, Amsterdam, 2012), vol. 5, pp. 168-182.
23. R. Rios, A. Cordova, in Comprehensive Chirality, E. M. Carreira, H. Yamamoto, Eds. (Elsevier, Amsterdam, 2012), vol. 6, pp. 399-413.
24. J. C. Bottaro, J. Chem. Soc. Chem. Commun. 1980, 560 (1980).
25. S. Andreae, E. Schmitz, Synthesis 1991, 327-341 (1991).
26. E. Vedejs, H. Sano, Tetrahedron Lett. 33, 3261-3264 (1992).
27. C.-M. Ho, T.-C. Lau, H.-L. Kwong, W.-T. Wong, J. Chem. Soc. Dalton Trans. 1999, 2411-2414 (1999).
28. A. Koohang, C. L. Stanchina, R. M. Coates, Tetrahedron 55, 9669-9686 (1999).
29. H. Lebel, S. Lectard, M. Parmentier, Org. Lett. 9, 4797-4800 (2007).
30. Z. Lu, Y. Zhang, W. D. Wulff, J. Am. Chem. Soc. 129, 7185-7194 (2007).
31. C. Varszegi et al., Angew. Chem. Int. Ed. 47, 1477-1480 (2008).
32. C. Zhu, G. Li, D. H. Ess, J. R. Falck, L. Kürti, J. Am. Chem. Soc. 134, 18253-18256 (2012).
33. C. G. Espino, K. W. Fiori, M. Kim, J. Du Bois, J. Am. Chem. Soc. 126, 15378-15379 (2004).
34. H. M. L. Davies, J. R. Manning, Nature 451, 417-424 (2008).
35. D. N. Zalatan, J. Du Bois, Top. Curr. Chem. 292, 347-378 (2010).
36. H. Lebel, in Catalyzed Carbon-Heteroatom Bond Formation, A. K. Yudin, Ed. (Wiley-VCH, Weinheim, Germany, 2011), pp. 137-155.
37. H. Lebel, K. Huard, S. Lectard, J. Am. Chem. Soc. 127, 14198-14199 (2005).
38. M. J. Frisch et al., Gaussian 09, Revision B.01; Gaussian, Wallingford, CT, 2009.
39. X. Lin, C. Zhao, C.-M. Che, Z. Ke, D. L. Phillips, Chem. Asian J. 2, 1101-1108 (2007).
40. R. Lorpitthaya, Z.-Z. Xie, K. B. Sophy, J.-L. Kuo, X.-W. Liu, Chemistry 16, 588-594 (2010).
41. L. Maestre, W. M. C. Sameera, M. M. Díaz-Requejo, F. Maseras, P. J. Pérez, J. Am. Chem. Soc. 135, 1338-1348 (2013).