Enantioselective desymmetrization of meso-aziridines with TMSN3 or TMSCN catalyzed by discrete yttrium complexes

Angewandte Chemie - International Edition

Volumn 48, Issue 6, 2009, Pages 1126-1129

  Wu, Bin ^a   Gallucci, Judith C ^a   Parquette, Jon R ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

Asymmetric catalysis; Aziridines; Ring opening; Yttrium

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; CHEMICAL REACTIONS; YTTRIUM;

ASYMMETRIC CATALYSIS; AZIRIDINES; DESYM-METRIZATION; DIMETALLIC MECHANISMS; ENANTIOSELECTIVE; RING-OPENING; SALEN COMPLEXES; SOLID-STATE STRUCTURES; YTTRIUM COMPLEXES;

YTTRIUM ALLOYS;

EID: 59049103335     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804415     Document Type: Article

References (37)

1. W. A. Nugent, J. Am. Chem. Soc. 1992, 114, 2768.
2. a) E. N. Jacobsen, Acc. Chem. Res. 2000, 33, 421;
3. b) B. M. Cole, K. D. Shimizu, C. A. Krueger, J. P. A. Harrity, M. L. Snapper, A. H. Hoveyda, Angew. Chem. 1996, 108, 1776;
4. Angew. Chem. Int. Ed. Engl. 1996, 35, 1668;
5. c) S. E. Schaus, B. D. Brandes, J. F. Larrow, M. Tokunaga, K. B. Hansen, A. E. Gould, M. E. Furrow, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 1307;
6. d) C. Schneider, A. R. Sreekanth, E. Mai, Angew. Chem. 2004, 116, 5809;
7. Angew. Chem. Int. Ed. 2004, 43, 5691;
8. e) K. Arai, S. Lucarini, M. M. Salter, K. Ohta, Y. Yamashita, S. Kobayashi, J. Am. Chem. Soc. 2007, 129, 8103, and references therein.
9. a) S. Matsubara, T. Kodama, K. Utimoto, Tetrahedron Lett. 1990, 31, 6379;
10. b) Z. Zhang, R. Scheffold, Helv. Chim. Acta 1993, 76, 2602;
11. c) M. Hayashi, K. Ono, H. Hoshimi, N. Oguni, J. Chem. Soc. Chem. Commum. 1994, 2699;
12. d) M. Hayashi, K. Ono, H. Hoshimi, N. Oguni, Tetrahedron 1996, 52, 7817;
13. e) P. Müller, P. Nury, Org. Lett. 1999, 1, 439;
14. f) Z. Li, M. Fernández, E. N. Jacobsen, Org. Lett. 1999, 1, 1611;
15. g) Y. Fukuta, T. Mita, N. Fukuda, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 6312;
16. h) I. Fujimori, T. Mita, K. Maki, M. Shiro, A. Sato, S. Furusho, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 16438;
17. i) E. B. Rowland, G. B. Rowland, E. Rivera-Otero, J. C. Antilla, J. Am. Chem. Soc. 2007, 129, 12084.
18. a) M.-H. Lin, T. V. RajanBabu, Org. Lett. 2000, 2, 997;
19. b) M.-H. Lin, T. V. RajanBabu, Org. Lett. 2002, 4, 1607;
20. c) M.-H. Lin, PhD Thesis, Ohio State University (USA), 2002.
21. B Saha, M.-H. Lin, T. V. RajanBabu, J. Org. Chem. 2007, 72, 8648.
22. S. E. Schaus, E. N. Jacobsen, Org. Lett. 2000, 2, 1001.
23. a) B. W. McCleland, W. A. Nugent, M. G. Finn, J. Org. Chem. 1998, 63, 6656;
24. similar models have been invoked by others to rationalize asymmetric induction in other metal-catalyzed transformations, for reviews, see: b) M. Kanai, N. Kato, E. Ichikawa, M. Shibasaki, Synlett 2005, 1491;
25. c) T. R. J. Achard, L. A. Clutterbuck, M. North, Synlett 2005, 1828.
26. a) For titanium examples, see: G. Boche, K. Möbus, K. Harms, M. Marsch, J. Am. Chem. Soc. 1996, 118, 2770;
27. 2 (several chloride bridged dimers): W. J. Evans, C. H. Fujimoto, J. W. Ziller, Chem. Commun. 1999, 311;
28. 2 (an hydroxide bridged dimer): C. M. Mascarenhas, S. P. Miller, P. S. White, J. P. Morken, Angew. Chem. 2001, 113, 621;
29. Angew. Chem. Int. Ed. 2001, 40, 601;
30. 2 (an alkoxide bridged dimer): T. M. Ovitt, G. W. Coates, J. Am. Chem. Soc. 2002, 124, 1316;
31. for CN-bridged complexes, see: e) C. E. Plecnik, S. Liu, S. S. Shore, Acc. Chem. Res. 2003, 36, 499;
32. f) S. Tanase, J. Reedijk, Coord. Chem. Rev. 2006, 250, 2501.
33. For a more complete list of complexes and the corresponding selectivities observed in the reaction shown in [Eq. (4)], see the Supporting Information.
34. O. Runte, T. Priermeier, R. Anwander, Chem. Commun. 1996, 1385.
35. S. L. McLain, T. M. Ford, N. E. Drysdale, Polym. Prep. 1992, 33, 463 (Am. Chem. Soc. Div. Polym. Chem.).
36. Curiously, when using catalyst 1a the enantioselectivity in the ring-opening reaction was depend on the solvent used for its preparation (see Table 1, entries 1 and 2). For example, the reaction carried out with the catalyst prepared in n-hexane gave an enantioselectivity of 52%ee (RR), whereas the catalyst prepared in THF gave 43%ee (SS), thus suggesting very subtle effects of aggregation.
37. See the Supporting information for the details of the X-ray crystallographic analysis of 4b. CCDC 701484 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data- request/cif. As the crystals form very thin plates, it was necessary to collect a data set by using a synchrotron. This data set was collected by Dr. Jeanette Krause through the SCrALS (Service Crystallography at Advanced Light Source) program at the Small-Crystal Crystallography Beamline 11.3.1 at the Advanced Light Source (ALS). The ALS is supported by the U.S. Department of Energy, Office of Energy Sciences, Materials Sciences Division, under contract DE-AC02-05CH11231 at Lawrence Berkeley National Laboratory.