The First Application of a Planar-Chiral Phosphorus Heterocycle in Asymmetric Catalysis: Enantioselective Hydrogenation of Dehydroamino Acids

Journal of Organic Chemistry

Volumn 63, Issue 13, 1998, Pages 4168-4169

  Qiao, Shuang ^a   Fu, Gregory C ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000565505     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980624b     Document Type: Article

References (24)

1. (a) Ruble, J. C.; Fu, G. C. J. Org. Chem. 1996, 61, 7230-7231.
2. (b) Ruble, J. C.; Latham, H. A.; Fu, G. C. J. Am. Chem. Soc. 1997, 119, 1492-1493.
3. (c) Ruble, J. C.; Tweddell, J.; Fu, G. C. J. Org. Chem. 1998, 63, 2794-2795.
4. (d) Liang, J.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1998, 63, 3154-3155.
5. (e) Garrett, C. E.; Fu, G. C. Submitted for publication.
6. Dosa, P. I.; Ruble, J. C.; Fu, G. C. J. Org. Chem. 1997, 62, 444-445.
7. (a) Nucleophilic catalysis (achiral): Garrett, C. E.; Fu, G. C. J. Org. Chem. 1997, 62, 4534-4535.
8. (b) Synthesis of an enantiopure diphosphaferrocene: Qiao, S.; Hoic, D. A.; Fu, G. C. Organometallics 1998, 17, 773-774.
9. Synthesized in two steps from commercially available compounds: Roman, E.; Leiva, A. M.; Casasempere, M. A.; Charrier, C.; Mathey, F.; Garland, M. T.; le Marouille, J.-Y. J. Organomet. Chem. 1986, 309, 323-332. See also ref 3a.
10. For a review of phospholide and phosphaferrocene chemistry, see: Mathey, F. Coord. Chem. Rev. 1994, 137, 1-52.
11. All yields in Figure 1 are the average of ≥ 2 runs.
12. For precedent with the Cp analogue of phosphaferrocene 2, see: de Lauzon, G.; Deschamps, B.; Fischer, J.; Mathey, F.; Mitschier, A. J. Am. Chem. Soc. 1980, 102, 994-1000.
13. Through Chromatographic separation of diastereomeric aminal derivatives: Ganter, C.; Brassat, L.; Ganter, B. Tetrahedron: Asymmetry 1997, 8, 2607-2611.
14. Ganter, C.; Brassat, L.; Ganter, B. Chem. Ber./Recueil 1997, 130, 1771-1776. Ganter prepared the racemic Cp analogue of 1 by a route that is somewhat different from that outlined in Figure 1. See also: Ganter, C.; Brassat, L.; Glinsböckel, C.; Ganter, B. Organometallics 1997, 16, 2862-2867. Deschamps, B.; Ricard, L.; Mathey, F. J. Organomet. Chem. 1997, 548, 17-22.
15. Ganter, C.; Brassat, L.; Ganter, B. Chem. Ber./Recueil 1997, 130, 1771-1776. Ganter prepared the racemic Cp analogue of 1 by a route that is somewhat different from that outlined in Figure 1. See also: Ganter, C.; Brassat, L.; Glinsböckel, C.; Ganter, B. Organometallics 1997, 16, 2862-2867. Deschamps, B.; Ricard, L.; Mathey, F. J. Organomet. Chem. 1997, 548, 17-22.
16. Ganter, C.; Brassat, L.; Ganter, B. Chem. Ber./Recueil 1997, 130, 1771-1776. Ganter prepared the racemic Cp analogue of 1 by a route that is somewhat different from that outlined in Figure 1. See also: Ganter, C.; Brassat, L.; Glinsböckel, C.; Ganter, B. Organometallics 1997, 16, 2862-2867. Deschamps, B.; Ricard, L.; Mathey, F. J. Organomet. Chem. 1997, 548, 17-22.
17. For recent examples, see: (a) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635-1636. (b) Chan, A. S. C.; Hu, W.; Pai, C.-C.; Lau, C.-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 129, 9570-9571. (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207-6208.
18. For recent examples, see: (a) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635-1636. (b) Chan, A. S. C.; Hu, W.; Pai, C.-C.; Lau, C.-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 129, 9570-9571. (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207-6208.
19. For recent examples, see: (a) Imamoto, T.; Watanabe, J.; Wada, Y.; Masuda, H.; Yamada, H.; Tsuruta, H.; Matsukawa, S.; Yamaguchi, K. J. Am. Chem. Soc. 1998, 120, 1635-1636. (b) Chan, A. S. C.; Hu, W.; Pai, C.-C.; Lau, C.-P.; Jiang, Y.; Mi, A.; Yan, M.; Sun, J.; Lou, R.; Deng, J. J. Am. Chem. Soc. 1997, 129, 9570-9571. (c) Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207-6208.
20. 2 symmetry.
21. 2 symmetry.
22. 2 symmetry.
23. 4) results in lower enantioselectivities.
24. 2-refill cycles, the valve to the Schlenk tube was closed. The reaction mixture was then stirred for 12 h at rt, at which time TLC indicated that all of the starting material had been consumed. The reaction mixture was concentrated and then passed through a short column (50:50 EtOAc/hexane). The ee was determined by chiral GC.