Enantioselective aziridination of cyclic enals facilitated by the fluorine-iminium ion Gauche effect

Chemistry - A European Journal

Volumn 20, Issue 3, 2014, Pages 794-800

  Molnár, István Gábor ^a   Tanzer, Eva Maria ^a   Daniliuc, Constantin ^a   Gilmour, Ryan ^a,b  

^a UNIVERSITY OF MÜNSTER   (Germany)

^b Cells in Motion ^*  (Germany)

Author keywords

aziridination; catalysis; enantioselectivity; fluorine; gauche effect; pre organisation

Indexed keywords

AMINO ACID DERIVATIVES; AZIRIDINATION; CONFORMATIONAL EFFECT; CRYSTALLOGRAPHIC ANALYSIS; FLUORINE SUBSTITUENTS; GAUCHE EFFECTS; PRE-ORGANISATION; REVERSIBLE FORMATION;

AMINO ACIDS; CATALYSIS; ENANTIOSELECTIVITY; IONS; ORGANIC COMPOUNDS; REACTION INTERMEDIATES;

FLUORINE;

AZIRIDINE DERIVATIVE; FLUORINE; ION; PYRROLIDINE; PYRROLIDINE DERIVATIVE;

ARTICLE; AZIRIDINATION; CATALYSIS; CHEMISTRY; CONFORMATION; ENANTIOSELECTIVITY; GAUCHE EFFECT; PRE-ORGANISATION; STATIC ELECTRICITY; STEREOISOMERISM; X RAY CRYSTALLOGRAPHY;

AZIRIDINATION; CATALYSIS; ENANTIOSELECTIVITY; FLUORINE; GAUCHE EFFECT; PRE-ORGANISATION;

AZIRIDINES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; FLUORINE; IONS; MOLECULAR CONFORMATION; PYRROLIDINES; STATIC ELECTRICITY; STEREOISOMERISM;

EID: 84892372246     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201303586     Document Type: Article

References (55)

1. R. Hili, A. K. Yudin, Chem. Eur. J. 2007, 13, 6538-6542
2. N. Assem, R. Hili, Z. He, T. Kasahara, B. L. Inman, S. Decker, A. K. Yudin, J. Org. Chem. 2012, 77, 5613-5623.
3. B. H. Rotstein, V. Rai, R. Hili, A. K. Yudin, Nat. Protoc. 2010, 5, 1813-1817
4. C. J. White, A. K. Yudin, Nat. Chem. 2011, 3, 509-513
5. L. L. W. Cheung, Z. He, S. M. Decker, A. K. Yudin, Angew. Chem. 2011, 123, 12002-12006
6. Angew. Chem. Int. Ed. 2011, 50, 11798-11802.
7. For selected examples of organocatalytic aziridination reactions using secondary amines see a) J. Vesely, I. Ibrahem, G.-L. Zhao, R. Rios, A. Cõrdova, Angew. Chem. 2007, 119, 792-795
8. Angew. Chem. Int. Ed. 2007, 46, 778-781
9. H. Arai, N. Sugaya, N. Sasaki, K. Makino, S. Lectard, Y. Hamada, Tetrahedron Lett. 2009, 50, 3329-3332
10. L. Deiana, G.-L. Zhano, S. Lin, P. Dziedzic, Q. Zhang, H. Leijonmarck, A. Cõrdova, Adv. Synth. Catal. 2010, 352, 3201-3207
11. H. Jinang, K. S. Halskov, T. K. Johansen, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 3842-3846
12. D. Worgull, G. Dickmeiss, K. L. Jensen, P. T. Franke, N. Holub, K. A. Jørgensen, Chem. Eur. J. 2011, 17, 4076-4080
13. L. Deiana, P. Dziedzic, G. L. Zhao, J. Vesely, I. Ibrahem, R. Rios, J. Sun, A. Cõrdova, Chem. Eur. J. 2011, 17, 7904-7917
14. A. Desmarchelier, D. P de Sant'Ana, V. Terrasson, J. M. Campagne, X. Moreau, C. Greck, R. M. de Figueiredo, Eur. J. Org. Chem. 2011, 4046-4052
15. K. S. Halskov, T. Naicker, M. E. Jensen, K. A. Jørgensen, Chem. Commun. 2013, 49, 6382-6384.
16. For selected examples of organocatalytic, enantioselective aziridination reactions see a) A. Armstrong, C. A. Baxter, S. G. Lamont, A. R. Pape, R. Wincewicz, Org. Lett. 2007, 9, 351-353
17. F. Pesciaioli, F. De Vincentiis, P. Galzerano, G. Bencivenni, G. Bartoli, A. Mazzanti, P. Melchiorre, Angew. Chem. 2008, 120, 8831-8834
18. Angew. Chem. Int. Ed. 2008, 47, 8703-8706
19. L. D. S. Yadav, R. K. Garima, Synlett 2009, 19, 3123-3126
20. F. De Vincentiis, G. Bencivenni, F. Pesciaioli, A. Mazzanti, G. Bartoli, P. Galzerano, P. Melchiorre, Chem. Asian J. 2010, 5, 1652-1656
21. H. Ren, W. D. Wulff, Org. Lett. 2010, 12, 4908-4911
22. H. Jiang, N. Holub, K. A. Jørgensen, Proc. Natl. Acad. Sci. USA 2010, 107, 20630-20635
23. A. K. Gupta, M. Mukherjee, W. D. Wulff, Org. Lett. 2011, 13, 5866-5869
24. L. Huang, W. D. Wulff, J. Am. Chem. Soc. 2011, 133, 8892-8895
25. C. De Fusco, T. Fuoco, G. Croce, A. Lattanzi, Org. Lett. 2012, 14, 4078-4081
26. Z. Chai, J.-P. Bouillon, D. Cahard, Chem. Commun. 2012, 48, 9471-9473.
27. For a seminal report see reference 3 a. For a review see, R. Chawla, A. K. Singh, L. D. S. Yadav, RSC Adv. 2013, 3, 11385-11403.
28. K.-H. Park, M. J. Kurth, Tetrahedron 2002, 58, 8629-8659.
29. C. Sparr, W. B. Schweizer, H. M. Senn, R. Gilmour, Angew. Chem. 2009, 121, 3111-3114
30. Angew. Chem. Int. Ed. 2009, 48, 3065-3068
31. C. Sparr, E.-M. Tanzer, J. Bachmann, R. Gilmour, Synthesis 2010, 1394-1397
32. C. Sparr, R. Gilmour, Angew. Chem. 2010, 122, 6670-6673
33. Angew. Chem. Int. Ed. 2010, 49, 6520-6523
34. E.-M. Tanzer, L. E. Zimmer, W. B. Schweizer and R. Gilmour, Chem. Eur. J. 2012, 18, 11334-11342
35. C. Sparr, L. E. Zimmer, R. Gilmour, in Asymmetric Syntheses. More Methods and Applications (Eds. , S. Bräse and M. Christmann,), Wiley-VCH, Weinheim, 2011, pp. 117-124
36. L. E. Zimmer, C. Sparr, R. Gilmour, Angew. Chem. 2011, 123, 12062-12074
37. Angew. Chem. Int. Ed. 2011, 50, 11860-11871.
38. For an excellent review see:, D. O'Hagan, Chem. Soc. Rev. 2008, 37, 308-319.
39. An example of the organocatalytic aziridination of a cyclic enal has been reported., A. Desmarchelier, V. Coeffard, X. Moreau, C. Greck, Chem. Eur. J. 2012, 18, 13222-13225. For an elegant report on the remote aziridination of cyclic 2,4-dienals see reference [3 h].
40. Compound 16 is commercially available. Enals 15, 17 and 18 (Table 4) were prepared according to a) V. Reutrakul, W. Kanghae, Tetrahedron Lett. 1977, 18, 1377-1380
41. H. Marschall, J. Penninger, P. Weyerstahl, Liebigs Ann. Chem. 1982, 49-67. Enals 19, 20 and 21 (Table 5) were prepared by adapting the procedure reported by
42. A. Naya, M. Ishikawa, K. Matsuda, K. Ohwaki, T. Saeki, K. Noguchi, N. Ohtake, Bioorg. Med. Chem. 2003, 11, 875-884.
43. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
44. C. McDonald, H. Holcomb, K. Kennedy, E. Kirkpatrick, T. Leathers, P. Vanemon, J. Org. Chem. 1989, 54, 1213-1215
45. Reactions using NBS gave lower yields. For an example see, Y. Xuan, H.-S. Lin, M. Yan, Org. Biomol. Chem. 2013, 11, 1815-1817.
46. B. A. Bhanu Prasad, G. Sekar, V. K. Singh, Tetrahedron Lett. 2000, 41, 4677-4679.
47. G. M. Alvernhe, C. E. Ennakoua, S. M. Lacombe, A. J. Laurent, J. Org. Chem. 1981, 46, 4938-4948. For a recent example of aziridine ring opening using chloride see reference [4 i].
48. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
49. G. Righi, S. Ciambrone, A. Pompili, F. Caruso, Tetrahedron Lett. 2007, 48, 7713-7716.
50. These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
51. For evidence of a fluorine-amine gauche effect see;, C. R. S. Briggs, M. J. Allen, D. O'Hagan, D. J. Tozer, A. M. Z. Slawin, A. E. Goeta, J. A. K. Howard, Org. Biomol. Chem. 2004, 2, 732-740
52. For evidence of a fluorine-imine gauche effect see, C. Sparr, E. Salamanova, W. B. Schweizer, H. M. Senn, R. Gilmour, Chem. Eur. J. 2011, 17, 8850-8857.
53. S. Routier, L. Saugé, N. Ayerbe, G. Coudert, J.-Y. Mérour, Tetrahedron Lett. 2002, 43, 589-591.
54. R. Hili, A. K. Yudin, Angew. Chem. 2008, 120, 4256-4259
55. Angew. Chem. Int. Ed. 2008, 47, 4188-4191.