Catalytic asymmetric aza-Darzens reaction with a vaulted biphenanthrol magnesium phosphate salt

Organic Letters

Volumn 13, Issue 9, 2011, Pages 2188-2191

  Larson, Shawn E ^a   Li, Guilong ^b   Rowland, Gerald B ^c   Junge, Denise ^a   Huang, Rongcai ^a   Woodcock, H Lee ^a   Antilla, Jon C ^a  

^a UNIVERSITY OF SOUTH FLORIDA   (United States)

^b SUN YAT SEN UNIVERSITY   (China)

^c MISSISSIPPI STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENANTHROL MAGNESIUM PHOSPHATE; HETEROCYCLIC COMPOUND; MAGNESIUM DERIVATIVE; MAGNESIUM PHOSPHATE; ORGANOPHOSPHATE; PHENANTHRENE DERIVATIVE; PHOSPHATE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

AZA COMPOUNDS; CATALYSIS; MAGNESIUM COMPOUNDS; MOLECULAR STRUCTURE; PHENANTHRENES; PHOSPHATES; PHOSPHORIC ACID ESTERS; STEREOISOMERISM;

EID: 79955637815     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol200407r     Document Type: Article

References (48)

1. Deyrup, J. A. J. Org. Chem. 1969, 34, 2624
2. For reviews, see: Yudin, A. K. Aziridines and Epoxides in Organic Synthesis; Wiley-VCH: Weinheim, Germany, 2006.
3. Masahiko, H.; Ono, K.; Hoshimi, H.; Oguni, N. Tetrahedron 1996, 52, 7817
4. Jacobsen, E. N. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 2, p 607.
5. Antilla, J. C.; Wulff, W. D. J. Am. Chem. Soc. 1999, 121, 5099
6. Antilla, J. C.; Wulff, W. D. Angew. Chem., Int. Ed. 2000, 39, 4518 For the background information for catalytic asymmetric aziridination before 1999, please see the cited references within these two papers.
7. Desai, A. A.; Wulff, W. D. J. Am. Chem. Soc. 2010, 132, 13104
8. McLaren, A. B.; Sweeney, J. B. Org. Lett. 1999, 1, 1339 For asymmetric aziridination with chiral sulfur ylides, see: Aggarwal, V. K.; Thompson, A.; Jones, R. V. H.; Standen, M. C. H. J. Org. Chem. 1996, 61, 8368
9. Aggarwal, V. K.; Alonso, E.; Fang, G.; Ferrara, M.; Hynd, G.; Porcelloni, M. Angew. Chem., Int. Ed. 2001, 40, 1433
10. Davis, F. A.; Liu, H.; Zhou, P.; Fang, T.; Reddy, G. V.; Zhang, Y. J. Org. Chem. 1999, 64, 7559
11. Williams, A. L.; Johnston, J. N. J. Am. Chem. Soc. 2004, 126, 1612 For a review of acid catalysis with diazoalkanes, see: Johnston, J.; Muchalski, H.; Troyer, T. L. Angew. Chem., Int. Ed. 2010, 49, 2290
12. Hashimoto, T.; Uchiyama, N.; Maruoka, K. J. Am. Chem. Soc. 2008, 130, 14380
13. Akiyama, T.; Suzuki, T.; Mori, K. Org. Lett. 2009, 11, 2445
14. Zeng, X.; Zeng, X.; Xu, Z.; Lu, M.; Zhong, G. Org. Lett. 2009, 11, 3036 For other recent examples, see: Giubellina, N.; Mangelinckx, S.; Törnroos, K. W.; De Kimpe, N. J. Org. Chem. 2006, 71, 5881
15. Valdez, C.; Leighton, J. J. Am. Chem. Soc. 2009, 131, 14638
16. Hashimoto, T.; Nakatsu, H.; Watanabe, S.; Maruoka, K. Org. Lett. 2010, 12, 1668
17. For select Mannich-type reactions with 1,3-dicarbonyl reagents, see: Hamashima, Y.; Sasamoto, N.; Hotta, D.; Somei, H.; Umebayashi, N.; Sodeoka, M. Angew. Chem., Int. Ed. 2005, 44, 1525
18. Song, J.; Wang, Y.; Deng, L. J. Am. Chem. Soc. 2006, 128, 6048
19. Chen, Z.; Morimoto, H.; Matsunaga, S.; Shibasaki, M. J. Am. Chem. Soc. 2008, 130, 2170
20. Hatano, M.; Maki, T.; Moriyama, K.; Arinobe, M.; Ishihara, K. J. Am. Chem. Soc. 2008, 130, 16858
21. Han, X.; Kwiatkowski, J.; Xue, F.; Huang, K.-W.; Lu, Y. Angew. Chem., Int. Ed. 2009, 48, 7604
22. Hatano, M.; Horibe, T.; Ishihara, K. J. Am. Chem. Soc. 2010, 132, 56
23. For pioneering chiral phosphoric-acid-catalyzed methods, see: Akiyama, T.; Itoh, J.; Yokota, K.; Fuchibe, K. Angew. Chem., Int. Ed. 2004, 43, 1566
24. Uraguchi, D.; Terada, M. J. Am. Chem. Soc. 2004, 126, 5356 For reviews with considerable chiral phosphoric acid coverage, see: Akiyama, T.; Itoh, J.; Fuchibe, K. Adv. Synth. Catal. 2006, 348, 999
25. Connon, S. Angew. Chem., Int. Ed. 2006, 45, 3909
26. Akiyama, T. Chem. Rev. 2007, 107, 5744
27. Terada, M. Chem. Commun. 2008, 4097
28. Adair, G.; Mukherjee, S.; List, B. Aldrichchim. Acta. 2008, 41, 31
29. Terada, M. Bull. Chem. Soc. Jpn. 2010, 83, 101
30. Hatano, M.; Moriyama, K.; Maki, T.; Ishihara, K. Angew Chem., Int. Ed. 2010, 49, 3823
31. Hatano, M.; Ikeno, T.; Matsumura, T.; Torii, S.; Ishihara, K. Adv. Synth. Catal. 2008, 350, 1776
32. Shen, K.; Liu, X.; Cai, Y.; Lin, L.; Feng, X. Chem.-Eur. J. 2009, 15, 6008
33. Klussmann, M.; Ratjen, L.; Hoffmann, S.; Wakchaure, V.; Goddard, R.; List, B Synlett 2010, 2189
34. Lv, J.; Li, X.; Zhong, L.; Luo, S.; Cheng, P. Org. Lett. 2010, 12, 1096
35. Rueping, M.; Koenigs, R. M.; Atodiresei, I. Chem.-Eur. J. 2010, 16, 9350
36. Rueping, M.; Nachtsheim, B. J.; Koenigs, R. M.; Ieawsuwan, W. Chem.-Eur. J. 2010, 16, 13116
37. Drouet, F.; Lalli, C.; Liu, H.; Masson, G.; Zhu, J. Org. Lett. 2011, 13, 94
38. Zhang, Z.; Zheng, W.; Antilla, J. C. Angew. Chem., Int. Ed. 2011, 50, 1135
39. Shao, Y. Phys. Chem. Chem. Phys. 2006, 8, 3172 For the full reference, see Supporting Information.
40. Becke, A. D. Phys. Rev. A 1988, 38, 3098
41. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785
42. Gill, P. M. W.; Johnson, B. G.; Pople, J. A.; Frisch, M. J. Chem. Phys. Lett. 1992, 197, 499-505
43. Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650
44. These structures were calculated for the R enantiomer of VAPOL, and negligible energy differences were noticed when the opposite enantiomer was calculated in similar work: Simon, L.; Goodman, J. J. Am. Chem. Soc. 2008, 130, 8741
45. NBO, version 5.0; Glendening, E. D.; Badenhoop, J, K.; Reed, A. E.; Carpenter, J. E.; Bohmann, J. A.; Morales, C. M.; Weinhold, F. Theoretical Chemistry Institute, University of Wisconsin, Madison, WI, 2001.
46. Simon, L.; Goodman, J. J. Am. Chem. Soc. 2009, 131, 4070
47. Terada, M.; Sorimachi, K.; Uraguchi, D. Synlett 2006, 133
48. Additional details are in the Supporting Information.