Assembly state of catalytic modules as chiral switches in asymmetric strecker amino acid synthesis

Journal of the American Chemical Society

Volumn 128, Issue 21, 2006, Pages 6768-6769

  Kato, Nobuki ^a   Mita, Tsuyoshi ^a   Kanai, Motomu ^a   Therrien, Bruno ^a,d   Kawano, Masaki ^a   Yamaguchi, Kentaro ^b   Danjo, Hiroshi ^b   Sei, Yoshihisa ^b   Sato, Akihiro ^c   Furusho, Sanae ^c   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^c Hachioji shi   (Japan)

^d UNIVERSITY OF NEUCHÂTEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALZHEIMER DISEASE; ARTICLE; CATALYSIS; CATALYST; CHIRALITY; COLOR; CREUTZFELDT JAKOB DISEASE; CRYSTAL STRUCTURE; DEGENERATIVE DISEASE; ELECTROSPRAY MASS SPECTROMETRY; ENANTIOSELECTIVITY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

AMINO ACIDS; CATALYSIS; CHEMISTRY, ORGANIC; CRYSTALLIZATION; MOLECULAR STRUCTURE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEREOISOMERISM; X-RAY DIFFRACTION;

EID: 33744830047     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja060841r     Document Type: Article

References (17)

1. Dobson, C. M. Nature 2003, 426, 884.
2. For example, see: Kato, T.; Mizoshita, N.; Kishimoto, K. Angew. Chem., Int. Ed. 2006, 45, 38.
3. Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491.
4. (a) Masumoto, S.; Usuda, H.; Suzuki, M.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2003, 125, 5634.
5. (b) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3147.
6. (c) Kato, N.; Suzuki, M.; Kanai, M.; Shibasaki, M. Tetrahedron Lett. 2004, 45, 3153.
7. Catalytic enantioselective Strecker reaction of ketoimines reported from other groups, see: (a) Vachal, P.; Jacobsen, E. N. Org. Lett. 2000, 2, 867.
8. (b) Vachal, P.; Jacobsen, E. N. J. Am. Chem. Soc. 2002, 124, 10012.
9. (c) Chavarot, M.; Byrne, J. J.; Chavant, P. Y.; Vallée, Y. Tetrahedron: Asymmetry 2001, 12, 1147.
10. See Supporting Information (SI) for details. For advantages in using Gd*-2 to Gd-2, see: (a) Fukuda, N.; Sasaki, K.; Sastry, T. V. R. S.; Kanai, M.; Shibasaki, M. J. Org. Chem. 2006, 71, 1220.
11. (b) Suzuki, M.; Kato, N.; Kanai, M.; Shibasaki, M. Org. Lett. 2005, 7, 2527.
12. For detailed X-ray and MS data, see SI.
13. Studies to elucidate the complex structures in solution using NMR did not give any useful information even when nonparamagnetic metals such as Y or La were used (no significant signals were observed).
14. 3, which contain both the 2:3 and 4:5+oxo complexes (Table 1).
15. For reviews, see (a) Buünzli, J. G.; Piguet, C. Chem. Rev. 2002, 102, 1897.
16. (b) Aspinall, H. C. Chem. Rev. 2002, 102, 1807.
17. The lower enantioselectivity of crystal B than that of Gd-1 or 2 might be due to differences in the metal character and not to the basic structure of the catalytically active subunit. Very similar ESI-QFT-MS fragment patterns were observed from crystal B, Gd-1, and Gd-2. See SI.