Catalytic asymmetric diaziridination

Journal of the American Chemical Society

Volumn 135, Issue 12, 2013, Pages 4692-4695

  Lykke, Lennart ^a   Halskov, Kim Søholm ^a   Carlsen, Bjørn Dreiø ^a   Chen, Victor X ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINATION; DIASTEREOMERS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIO; N-TOSYL ALDIMINES; OPTICALLY ACTIVE; PHASE TRANSFER CATALYSIS;

CHEMISTRY; SYNTHESIS (CHEMICAL);

REACTION KINETICS;

AZIRIDINE DERIVATIVE; DIAZIRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; COVALENT BOND; CYCLIZATION; ENANTIOSELECTIVITY; NUCLEOPHILICITY; SYNTHESIS;

EID: 84875713135     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja401150m     Document Type: Article

References (49)

1. Asymmetric Synthesis of Nitrogen Heterocycles; Royer, J., Ed.; Wiley-VCH: Wienheim, 2009.
2. Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006.
3. Schmitz, E. Adv. Heterocycl. Chem. 1979, 24, 63
4. Schmitz, E. In Diaziridines, 3H-Diazirines, Diaziridinones and Diaziridinimines, Small Ring Heterocycles, Vol. 1; Lowowski, W., Ed.; Pergamon Press: Oxford, 1983; p 195.
5. Schmitz, E. Angew. Chem. 1959, 71, 127
6. Abendroth, H. J.; Henrich, G. Angew. Chem. 1959, 71, 283
7. Paulsen, S. R. Belg. Pat. 1959, 588352
8. Kostyanovsky, R. G.; Murugan, R.; Sutharchanadevi, M. In Comprehensive Heterocyclic Chemistry II, Vol. 1A; Padwa, A., Ed.; Elsevier: Oxford, 1996; p 347.
9. McAllister, G. D.; Perry, A.; Taylor, R. J. K. In Comprehensive Heterocyclic Chemistry III, Vol. 1; Padwa, A., Ed.; Elsevier: New York, 2008; p 539.
10. Makhova, N. N.; Shevtsov, A. V.; Petukhova, V. Y. Russ. Chem. Rev. 2011, 80, 1035
11. Jennings, W. B.; Boyd, D. R. In Cyclic Organonitrogen Stereodynamics; Lambert, J. B.; Takeuchi, Y., Eds.; VCH: New York, 1992; Chapter 5.
12. Ishihara, H.; Hori, K.; Sugihara, H.; Ito, Y. N.; Katsuki, T. Helv. Chim. Acta 2002, 85, 4272
13. Komatsu, M.; Nishikaze, N.; Sakamoto, M.; Oshihiro, Y.; Agawa, T. J. Org. Chem. 1974, 39, 3198
14. Shevtsov, A. V.; Kuznetsov, V. V.; Kislukhin, A. A.; Petukhova, V. Y.; Strelenko, Y. A.; Makhova, N. N. J. Heterocycl. Chem. 2006, 43, 881
15. Syroeshkina, Y. S.; Kuznetsov, V. V.; Lyssenko, K. A.; Makhova, N. N. Mendeleev Commun. 2008, 18, 207
16. Alper, H.; Delledonne, D.; Kameyama, M.; Roberto, D. Organometallics 1990, 9, 762
17. Du, H.; Zhao, B.; Shi, Y. J. Am. Chem. Soc. 2007, 129, 762
18. Zhao, B.; Du, H.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 3523
19. Zhao, B.; Peng, X.; Cui, S.; Shi, Y. J. Am. Chem. Soc. 2010, 132, 11009
20. Capretto, D. A.; Brouwer, C.; Poor, C. B.; He, C. Org. Lett. 2011, 13, 5842
21. Moss, R. A. Acc. Chem. Res. 2006, 39, 267
22. Hashimoto, M.; Hatanaka, Y. Eur. J. Org. Chem. 2008, 2513
23. For a review of the synthesis of diaziridines, see: Makhova, N. N.; Petukhova, V. Y.; Kuznetsov, V. V. ARKIVOC 2008, 128
24. Fioravanti, S.; Olivieri, L.; Pellacani, L.; Tardella, P. A. Tetrahedron Lett. 1998, 39, 6391
25. Carroccia, L.; Fioravanti, S.; Pellacani, L.; Sadun, C.; Tardella, P. A. Tetrahedron 2011, 67, 5375
26. Carroccia, L.; Delfini, M.; Fioravanti, S.; Pellacani, L.; Sciubba, F. J. Org. Chem. 2012, 77, 2069
27. Rowland, G. B.; Zhang, H.; Rowland, E. B.; Chennamadhavuni, S.; Wang, Y.; Antilla, J. C. J. Am. Chem. Soc. 2005, 127, 15696
28. Vesely, J.; Ibrahem, I.; Zhao, G.-L.; Rios, R.; Córdova, A. Angew. Chem., Int. Ed. 2007, 46, 778
29. Deiana, L.; Dziedzic, P.; Zhao, G.-L.; Vesely, J.; Ibrahem, I.; Rios, R.; Sun, J.; Córdova, A. Chem.-Eur. J. 2011, 17, 7904
30. Pesciaioli, F.; Vincentiis, F. D.; Galzerano, P.; Bencivenni, G.; Bartoli, G.; Mazzanti, A.; Melchiorre, P. Angew. Chem., Int. Ed. 2008, 47, 8703
31. Arai, H.; Sugaya, N.; Sasaki, N.; Makino, K.; Lectard, S.; Hamada, Y. Tetrahedron Lett. 2009, 50, 3329
32. Jiang, H.; Holub, N.; Jørgensen, K. A. Proc. Natl. Acad. Sci. U.S.A. 2010, 107, 20630
33. Albrecht, L.; Jiang, H.; Dickmeiss, G.; Geschwend, B.; Hansen, S. G.; Jørgensen, K. A. J. Am. Chem. Soc. 2010, 132, 9188
34. Jiang, H.; Halskov, K. S.; Johansen, T. K.; Jørgensen, K. A. Chem.-Eur. J. 2011, 17, 3842
35. Ooi, T.; Maruoka, K. Angew. Chem., Int. Ed. 2007, 46, 4222
36. Hashimoto, T.; Maruoka, K. Chem. Rev. 2007, 107, 5656
37. Brak, K.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2013, 52, 534
38. Asymmetric Phase Transfer Catalysis; Maruoka, M., Ed.; Wiley-VCH: Wienheim, 2008. For recent examples, see
39. He, R.; Shirakawa, S.; Maruoka, K. J. Am. Chem. Soc. 2009, 131, 16620
40. Ma, T.; Fu, X.; Kee, C. W.; Zong, L.; Pan, Y.; Huang, K.-W.; Tan, C.-H. J. Am. Chem. Soc. 2011, 133, 2828
41. Shirakawa, S.; Liu, K.; Maruoka, K. J. Am. Chem. Soc. 2012, 134, 916
42. Hong, S.; Lee, J.; Kim, M.; Park, Y.; Park, C.; Kim, M.-H.; Jew, S.-S.; Park, H.-G. J. Am. Chem. Soc. 2011, 133, 4924
43. Qi, J.; Beeler, A. B.; Zhang, Q.; Porco, J. A. J. Am. Chem. Soc. 2010, 132, 13642
44. For X-ray analysis details, see Supporting Information. Ortep-3 was used for the X-ray plot: Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565
45. Calculations were performed with GAUSSIAN09. Geometries were optimized without symmetry constraints at the M06-2X/6-31+G(d,p) level of theory (Zhao, Y.; Truhlar, D. Theor. Chem. Acc. 2008, 120, 215) in the gas phase. See Supporting Information for the details and references for theoretical methods
46. Nielsen, I. M. B. J. Phys. Chem. A 1998, 102, 3193
47. Alkorta, I.; Elguero, J.; Zborowski, K. J. Phys. Chem. A 2007, 111, 1096
48. Nyasse, B.; Grehn, L.; Ragnarsson, U. Chem. Commun. 1997, 1017
49. Angle, S. R.; Henry, R. H. J. Org. Chem. 1998, 63, 7490