Enantioselective cyanoformylation of aldehydes mediated by BINOLAM-AlCl as a monometallic bifunctional catalyst

Tetrahedron Asymmetry

Volumn 14, Issue 2, 2003, Pages 197-200

  Casas, Jesús ^a   Baeza, Alejandro ^a   Sansano, José M ^a   Nájera, Carmen ^a   Saá, José M ^b  

^a UNIVERSITY OF ALICANTE   (Spain)

^b UNIVERSITAT DE LES ILLES BALEARS   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; CYANOHYDRIN; FORMIC ACID DERIVATIVE; LEWIS ACID; NAPHTHALENE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CATALYST; CHEMICAL REACTION; CYANOFORMYLATION; ENANTIOMER; ENANTIOSELECTIVITY; GAS CHROMATOGRAPHY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE;

EID: 0037449604     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(02)00824-8     Document Type: Article

References (30)

1. (a) Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E. Houben-Weyl, Methods of Organic Chemistry, Stereoselective Synthesis; Thieme: Stuttgart/New York, 1996; Vol. E21
2. (b) Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000
3. (c) Comprehensive Asymmetric Catalysis I-III; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Eds.; Springer Verlag: Berlin, 1999.
4. (d) Corey E.J., Helal C.J. Angew. Chem., Int. Ed. 37:1998;1987-2012
5. (e) Asymmetric Catalysis in Organic Synthesis; Noyori, R., Ed.; Wiley: New York 1994.
6. Shibasaki M., Kanai M., Funabashi K. Chem. Commun. 2002;1989-1999.
7. Matsunaga S., Ohshima T., Shibasaki M. Adv. Synth. Catal. 344:2002;3-9.
8. Shibasaki M., Kanai M. Chem. Pharm. Bull. 49:2001;511-524.
9. Rowlands G.J. Tetrahedron. 57:2001;1865-1882.
10. Gröger H. Chem. Eur. J. 7:2001;5246-5251.
11. Hamashima Y., Sawada D., Kanai M., Shibasaki M. J. Am. Chem. Soc. 121:1999;2641-2642.
12. Hamashima Y., Sawada D., Nogami H., Kanai M., Shibasaki M. Tetrahedron. 57:2001;805-814.
13. Takamura M., Hamashima Y., Usuda H., Kanai M., Shibasaki M. Angew. Chem., Int. Ed. 39:2000;1650-1652.
14. Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 122:2000;6327-6328.
15. Takamura M., Funabashi K., Kanai M., Shibasaki M. J. Am. Chem. Soc. 123:2001;6801-6808.
16. Casas J., Nájera C., Sansano J.M., Saá J.M. Org. Lett. 4:2002;2589-2592.
17. Scholl M., Lim C.-K., Fu G.C. J. Org. Chem. 60:1995;6229-6231.
18. Shin D.-S., Jung Y.S., Kim J.-J., Ahn C. Bull. Korean Chem. Soc. 19:1998;119-120.
19. Berthiaume D., Poirier D. Tetrahedron. 56:2000;5995-6003.
20. Deardorff D.R., Taniguchi C.M., Tafti S.A., Kim H.Y., Choi S.Y., Downey K.J., Nguyen T.V. J. Org. Chem. 66:2001;7191-7194.
21. Okimoto M., Chiba T. Synthesis. 1996;1188-1190.
22. Tian S.-K., Deng L. J. Am. Chem. Soc. 123:2001;6195-6196.
23. Tian J., Yamagiwa N., Matsunaga S., Shibasaki M. Angew. Chem., Int. Ed. 41:2002;3636-3638.
24. 2O donor has been demonstrated in the case of binaphthol-derived titanium complexes: Terada M., Matsumoto Y., Nakamura Y., Mikami K. Chem. Commun. 1997;281-282.
25. 3PO to prevent oligomerisation of the catalyst and to activate trimethylsilyl cyanide has been pointed out by: Vogl E.M., Gröger H., Shibasaki M. Angew. Chem., Int. Ed. 38:1999;1570-1577.
26. 4) and evaporated, affording the pure crude product 4.
27. Aoi T., Kagoshima K., Maruoka K. J. Am. Chem. Soc. 119:1997;5754-5755.
28. The X-ray structure of the pentacoordinate BINOL-AlMe(THF) dimmer complex has been described: Arai T., Sasai H., Yamaguchi K., Shibasaki M. J. Am. Chem. Soc. 120:1998;441-442.
29. Corey E.J., Lee T.W. Chem. Commun. 2001;1321-1329.
30. Deardorff D.R., Taniguchi C.M., Tafti S.A., Kim H.Y., Choi S.Y., Downey K.J., Nguyen T.V. J. Org. Chem. 66:2001;7191-7194.