Key role of the Lewis base position in asymmetric bifunctional catalysis: Design and evaluation of a new ligand for chiral polymetallic catalysts

Journal of the American Chemical Society

Volumn 128, Issue 51, 2006, Pages 16438-16439

  Fujimori, Ikuo ^a   Mita, Tsuyoshi ^a   Maki, Keisuke ^a   Shiro, Motoo ^b   Sato, Akihiro ^c   Furusho, Sanae ^c   Kanai, Motomu ^a   Shibasaki, Masakatsu ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b RIGAKU CORPORATION   (Japan)

^c Hachioji shi   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINE DERIVATIVE; CYANIDE; GADOLINIUM; GLUCOSE; LEWIS BASE; LIGAND; METAL DERIVATIVE; POLYMER; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHELATION; CHIRALITY; CRYSTAL STRUCTURE; ENANTIOSELECTIVITY; RING OPENING; STOICHIOMETRY; SYNTHESIS;

AZIRIDINES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; LIGANDS; METALS, RARE EARTH; MODELS, MOLECULAR; MOLECULAR CONFORMATION; ORGANOMETALLIC COMPOUNDS; OXIDES; PHOSPHINES; STEREOISOMERISM;

EID: 33845944635     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067003h     Document Type: Article

References (11)

1. (a) Shibasaki, M.; Sasai, H.; Aral. T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236.
2. (b) Kanai, M.; Kato, N.; Ichikawa, E.; Shibasaki, M. Synlett 2005, 1491.
3. Kato, N.; Mita, T.; Kanai, M.; Therrien, B.; Kawano, M.; Yamaguchi, K.; Danjo, H.; Sei, Y.; Sato, A.; Furusho, S.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6768.
4. (a) Lüssem, B. J.; Gais, H.-J. J. Am. Chem. Soc. 2003, 125, 6066.
5. (b) Trost, B. M.; Organ, M. G. J. Am. Chem. Soc. 1994, 116, 10320.
6. On the other hand, synthesis of 3 requires eight steps (overall yield = 37%) from a commercially available compound. See, Kato, N.; Tomita, D.; Maki, K.; Kanai, M.; Shibasaki M. J. Org. Chem. 2004, 69, 6128.
7. Mita, T.; Fujimori, I.; Wada, R.; Wen, J.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2005, 127, 11252.
8. For reviews, see: (a) Abele, S.; Seebach, D. Eur. J. Org. Chem. 2000, 1.
9. (b) Gellman, S. H. Acc. Chem. Res. 1998, 31, 173.
10. See Supporting Information for details.
11. For example, the reaction of 13a was completed at room temperature in 4 h and in 15 min using 10 mol % of catalyst derived from 3 and 7, respectively.