Asymmetric synthesis of O-benzoyl cyanohydrins by reaction of aldehydes with benzoyl cyanide catalysed by BINOLAM-Ti(IV) complexes

Tetrahedron Asymmetry

Volumn 16, Issue 14, 2005, Pages 2385-2389

  Baeza, Alejandro ^a   Nájera, Carmen ^a   Sansano, José M ^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

3,3' BIS(DIETHYLAMINOMETHYL) 1,1' BINAPHTHOL; ALDEHYDE; BASE; CYANIDE; CYANOHYDRIN; LEWIS ACID; NAPHTHOL DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CYANATION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PRIORITY JOURNAL; ROOM TEMPERATURE;

EID: 23044482263     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.05.031     Document Type: Article

References (48)

1. For general applications and asymmetric synthesis of cyanohydrins and their derivatives, see: M. North Synthesis and Applications of Non-racemic Cyanohydrins and α-Amino Acids Tetrahedron Sympos. 60 2004 10371 10568
2. J.-M. Brunel, and I.P. Holmes Angew. Chem., Int. Ed. 116 2004 2810 2837
3. M. North Tetrahedron: Asymmetry 14 2003 147 176
4. Vachal, P.; Jacobsen, E. N. In Jacobsen, E. N.; Pfaltz, A.; Yamamoto H., Eds.; Comprehensive Asymmetric Catalysis. Supplement 1, pp 117-129.
5. R.J.H. Gregory Chem. Rev. 99 1999 3649 3682
6. F. Effenberger Angew. Chem. 106 1994 1609 1619
7. M. North Synlett 1993 807 820
8. T. Purkarthofer, W. Skranc, H. Weber, H. Griengl, M. Wubbolts, G. Scholz, and P. Pöchlauer Tetrahedron 60 2004 735 739
9. G. Seoane Curr. Org. Chem. 4 2000 283 304
10. M. Schmidt, and H. Griengl Top. Curr. Chem. 200 1999 193 226
11. F. Effenberger Chimia 53 1999 3 10
12. S.-K. Tian, and L. Deng J. Am. Chem. Soc. 123 2001 6195 6196
13. N. Yamahiwa, J. Tian, S. Matsunaga, and M. Shibasaki J. Am. Chem. Soc. 127 2005 3413 3422
14. J. Tian, N. Yamagiwa, S. Matsunaga, and M. Shibasaki Org. Lett. 5 2003 3021 3024
15. J. Tian, N. Yamagiwa, S. Matsunaga, and M. Shibasaki Angew. Chem., Int. Ed. 41 2002 3636 3638
16. Y.N. Belokon', A.J. Blacker, P. Carta, L.A. Clutterbuck, and M. North Tetrahedron 60 2004 10433 10447
17. Y.N. Belokon', A.J. Blacker, L.A. Clutterbuck, and M. North Org. Lett. 5 2003 4505 4507
18. (a) J. Casas, A. Baeza, J.M. Sansano, C. Nájera, and J.M. Saá Tetrahedron: Asymmetry 14 2003 197 200
19. A. Baeza, C. Nájera, J.M. Sansano, and J.M. Saá Angew. Chem., Int. Ed. 42 2003 3143 3146
20. A. Baeza, C. Nájera, J.M. Sansano, and J.M. Saá Chem. Eur. J. 11 2005 3849 3862
21. Y. Abiko, N. Yamahiwa, M. Sugita, J. Tian, S. Matsunaga, and M. Shibasaki Synlett 2004 2434 2436
22. Y.N. Belokon', P. Carta, A.V. Gutnov, V. Maleev, M.A. Moskalenko, L.V. Yashkina, N.S. Ikonnikov, N.V. Voskoboev, V.N. Khrustalev, and M. North Helv. Chim. Acta 85 2002 3301 3312
23. Y.N. Belokon', A.V. Gutnov, M.A. Moskalenko, L.V. Yashkina, D.E. Lesovoy, N.S. Ikonnikov, V. Larichev, and M. North Chem. Commun. 2002 244 245
24. Y.N. Belokon', P. Carta, and M. North Lett. Org. Chem. 1 2004 81 83
25. Y.N. Belokon', P. Carta, A.V. Gutnov, V. Malcev, M.A. Moskalenko, L.V. Yashkina, N.S. Ikonnikov, N.V. Boskoboev, V.N. Khrustalev, and M. North Helv. Chim. Acta 85 2002 3301 3312
26. W. Huang, Y. Song, C. Bai, G. Cao, and Z. Zheng Tetrahedron Lett. 45 2004 4763 4767
27. The racemic synthesis of O-acyl cyanohydrins is very well known from aldehydes and acetyl or aroyl cyanides: by the DABCO-mediated synthesis H.M.R. Hoffmann, Z.M. Ismail, R. Hollweg, and A.R. Zein Bull. Chem. Soc. Jpn. 63 1990 1807 1810
28. by using substoichiometric amounts of tri-n-butyltin cyanide M. Scholl, C.-K. Lim, and G. Fu J. Org. Chem. 60 1995 6229 6231
29. and in aqueous media using potassium carbonate M. Okimoto, and T. Chiba Synthesis 1996 1188 1190
30. For synthetic applications of (S)- and (R)-BINOLAM 3, see: As suitable phase-transfer catalysts for the enantioselective alkylation of the aldimine Schiff bases of alanine esters, see: J. Casas, C. Nájera, J.M. Sansano, J. González, J.M. Saá, and M. Vega Tetrahedron: Asymmetry 12 2001 699 702
31. In the addition of diethylzinc to aldehydes, see: H. Kitajima, K. Iti, and T. Katsuki Chem. Lett. 1996 343 344
32. In the enantioselective Simmons-Smith cyclopropanation, see: H. Kitajima, K. Ito, and T. Katsuki Chem. Lett. 1995 1113 1114
33. In the enantioselective Michael addition, see: H. Kitajima, K. Ito, and T. Katsuki Tetrahedron 53 1997 17015 17028
34. For reviews about bifunctional catalysis, see: M. Shibasaki, M. Kanai, and K. Funabashi Chem. Commun. 2002 1189 1199
35. S. Matsunaga, T. Ohshima, and M. Shibasaki Adv. Synth. Catal. 344 2002 3 15
36. H. Gröger Chem. Eur. J. 7 2001 5246 5251
37. G.J. Rowlands Tetrahedron 57 2001 1865 1882
38. J. Casas, C. Nájera, J.M. Sansano, and J.M. Saá Org. Lett. 4 2002 2589 2592
39. J. Casas, C. Nájera, J.M. Sansano, and J.M. Saá Tetrahedron 60 2004 10487 10496
40. 4 and evaporated, to yield (S)-BINOLAM in 96% (11 mg).
41. S.-K. Ling, T. Tanaka, and I. Kouno J. Nat. Prod. 65 2002 131
42. D.J. Buchanan, D.J. Dixon, M.S. Scott, and D.I. Lainé Tetrahedron: Asymmetry 15 2004 195 197
43. B.T. Cho, S.K. Kang, and S.H. Shin Tetrahedron: Asymmetry 13 2002 1209 1217
44. J.S. Yadav, P.T. Reddy, S. Nanda, and A.B. Rao Tetrahedron: Asymmetry 12 2001 3381 3385
45. R.F.C. Brown, A.C. Donohue, W.R. Jackson, and T.D. McCarthy Tetrahedron 50 1994 13739 13752
46. R.F.C. Brown, W.R. Jackson, and T.D. McCarthy Tetrahedron: Asymmetry 4 1993 205 206
47. D.V. Johnson, U. Felfer, and H. Griengl Tetrahedron 56 2000 781 790
48. D.V. Johnson, and H. Griengl Tetrahedron 53 1997 617 624