Catalytic enantioselective aryl transfer: Asymmetric addition of boronic acids to aldehydes using pyrrolidinylmethanols as ligands

Tetrahedron Letters

Volumn 46, Issue 45, 2005, Pages 7827-7830

  Braga, Antonio L ^a   Lüdtke, Diogo S ^a   Schneider, Paulo H ^a   Vargas, Fabricio ^a   Schneider, Alex ^b   Wessjohann, Ludger A ^b   Paixão, Márcio W ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

^b LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

Asymmetric catalysis; Boronic acids; Diarylmethanols; Proline; Zinc

Indexed keywords

ALDEHYDE; BORONIC ACID DERIVATIVE; LIGAND; METHANOL DERIVATIVE; PROLINE; PYRROLIDINE DERIVATIVE; ZINC;

ARTICLE; CATALYSIS; DRUG STRUCTURE; ENANTIOSELECTIVITY;

EID: 26444476949     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.026     Document Type: Article

References (35)

1. K. Meguro, M. Aizawa, T. Sohda, A. Kawamatsu, and A. Nagaoka Chem. Pharm. Bull. 33 1985 3787
2. F. Toda, K. Tanaka, and K. Koshiro Tetrahedron: Asymmetry 2 1991 873
3. S. Stanev, R. Rakovska, N. Berova, and G. Snatzke Tetrahedron: Asymmetry 6 1995 183
4. M. Botta, V. Summa, F. Corelli, G. Di Pietro, and P. Lombardi Tetrahedron: Asymmetry 7 1996 1263
5. For leading references, see: K. Bolshan, C.-Y. Chen, J.R. Chilenski, F. Gosselin, D.J. Mathre, P.D. O'Shea, A. Roy, and R.D. Tillyer Org. Lett. 6 2004 111 and references cited therein
6. For asymmetric hydrogenation and oxazaborolidine reduction of benzophenones, see: T. Ohkuma, M. Koizume, H. Ikehira, T. Yokozawa, and R. Noyori Org. Lett. 2 2000 659
7. E.J. Corey, and C.J. Helal Angew. Chem., Int. Ed. 37 1998 1986
8. R. Noyori, and T. Ohkuma Angew. Chem., Int. Ed. 40 2001 40
9. R. Noyori Angew. Chem., Int. Ed. 41 2002 2008
10. C.-Y. Chen, R.A. Reamer, J.R. Chilenski, and C.J. McWilliams Org. Lett. 5 2003 5039
11. P.I. Dosa, J.C. Ruble, and G.C. Fu J. Org. Chem. 62 1997 444
12. W.-S. Huang, Q.-S. Hu, and L. Pu J. Org. Chem. 62 1999 7940
13. C. Bolm, and K. Muñiz Chem. Commun. 1999 1295
14. C. Bolm, N. Hermanns, J.P. Hildebrand, and K. Nuñiz Angew. Chem., Int. Ed. 39 2000 3465
15. G. Zhao, X.-G. Li, and X.-R. Wang Tetrahedron: Asymmetry 12 2001 399
16. J. Rudolph, N. Hermanns, and C. Bolm J. Org. Chem. 69 2004 3997
17. M. Fontes, X. Verdaguer, L. Solà, M.A. Pericàs, and A. Riera J. Org. Chem. 69 2004 2532
18. C. Bolm, F. Schmidt, and L. Zani Tetrahedron: Asymmetry 16 2005 1367
19. J. Rudolph, F. Schmidt, and C. Bolm Adv. Synth. Catal. 346 2004 867
20. C. Bolm, L. Zani, J. Rudolph, and I. Schiffers Synthesis 2004 2173
21. J.K. Park, H.G. Lee, C. Bolm, and B.M. Kim Chem. Eur. J. 11 2005 945
22. W.-S. Huang, and L. Pu Tetrahedron Lett. 41 2000 145
23. C. Bolm, and J. Rudolph J. Am. Chem. Soc. 124 2002 14850
24. O. Prieto, D.J. Ramón, and M. Yus Tetrahedron: Asymmetry 14 2003 1955
25. J.-X. Ji, J. Wu, T.T.-L. Au-Yeung, C.W. Yip, K.R. Haynes, and A.S.C. Chan J. Org. Chem. 70 2005 1093
26. J. Rudolph, F. Schmidt, and C. Bolm Synthesis 2005 840
27. For some representative examples, see: A.L. Braga, H.R. Appelt, P.H. Schneider, C.C. Silveira, and L.A. Wessjohann Tetrahedron: Asymmetry 10 1999 1733
28. A.L. Braga, M.W. Paixão, D.S. Lüdtke, C.C. Silveira, and O.E.D. Rodrigues Org. Lett. 5 2003 2635
29. A.L. Braga, P. Milani, M.W. Paixão, G. Zeni, O.E.D. Rodrigues, and E.F. Alves Chem. Commun. 2004 2488
30. A.L. Braga, D.S. Lüdtke, F. Vargas, and M.W. Paixão Chem. Commun. 2005 2512
31. For other applications, see: K. Soai, A. Ookawa, T. Kaba, and K. Ogawa J. Am. Chem. Soc. 109 1987 7111
32. G. Liu, and J.A. Ellman J. Org. Chem. 60 1995 7712
33. C.L. Gibson Tetrahedron: Asymmetry 10 1999 1551
34. +: 268.1696.
35. 4, filtered, and the solvents evaporated. Purification by flash chromatography eluting with a mixture of hexanes/ethyl acetate (90:10) afforded the pure diarylmethanols. HPLC-analyses: All measurements were performed at a 20°C column temperature using a UV detector at 254 nm. Phenyl(p-tolyl) methanol (4a ): Chiralcel OD, hexane/i-PrOH (90:10), 0.5 mL/min, (S): 19.1 min, (R): 21.1 min.