Lipase-catalysed resolution by an esterification reaction in organic solvent of axially chiral (±)-3,3′-bis(hydroxymethyl)-2,2′- bipyridine N,N-dioxide

Tetrahedron Asymmetry

Volumn 17, Issue 1, 2006, Pages 12-14

  Sanfilippo, Claudia ^a   D'Antona, Nicola ^a   Nicolosi, Giovanni ^a  

^a CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

3,3' BIS(HYDROXYMETHYL) 2,2' BIPYRIDINE N,N DIOXIDE; ALCOHOL; BIPYRIDINE DERIVATIVE; ORGANIC SOLVENT; UNCLASSIFIED DRUG; VINYL ACETATE;

ARTICLE; BURKHOLDERIA CEPACIA; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ESTERIFICATION; MUCOR; PRIORITY JOURNAL;

EID: 30944439078     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2005.11.028     Document Type: Article

References (23)

1. For recent reviews, see: A.V. Malkov, and P. Kočovskŷ Curr. Org. Chem. 7 2003 1737 1757
2. G. Chelucci, and R.P. Thummel Chem. Rev. 102 2002 3129 3170
3. N.C. Fletcher J. Chem. Soc., Perkin Trans. 1 2002 1831 1842
4. For a review on the synthesis and application in asymmetric catalysis of chiral pyridine N-oxides, see: G. Chelucci, G. Murineddu, and G.A. Pinna Tetrahedron: Asymmetry 15 2004 1373 1389
5. A.V. Malkov, M. Bell, F. Castelluzzo, and P. Kočovský Org. Lett. 7 2005 3219 3222
6. T. Shimada, A. Kina, and T. Hayashi J. Org. Chem. 68 2003 6329 6337
7. T. Shimada, A. Kina, S. Ikeda, and T. Hayashi Org. Lett. 4 2002 2799 2801
8. M. Nakajima, M. Saito, M. Shiro, and S. Hashimoto J. Am. Chem. Soc. 120 1998 6419 6420
9. M. Nakajima, M. Saito, M. Uemura, and S. Hashimoto Tetrahedron Lett. 43 2002 8827 8829
10. M. Nakajima, T. Yokota, M. Saito, and S. Hashimoto Tetrahedron Lett. 45 2004 61 64
11. S.E. Denmark, and Y. Fan J. Am. Chem. Soc. 124 2002 4233 4235
12. M. Tichý, J. Závada, J. Podlaha, and P. Vojtíšek Tetrahedron: Asymmetry 6 1995 1279 1282
13. M. Juarez-Hernandez, D.V. Johnson, H.L. Holland, J. McNulty, and A. Capretta Tetrahedron: Asymmetry 14 2003 289 291
14. M. Inagaki, J. Hiratake, T. Nishioka, and J. Oda Agric. Biol. Chem. 53 1989 1879 1884
15. C. Sanfilippo, G. Nicolosi, G. Delogu, D. Fabbri, and M.A. Dettori Tetrahedron: Asymmetry 14 2003 3267 3270
16. C. Sanfilippo, G. Nicolosi, G. Delogu, D. Fabbri, and M.A. Dettori Tetrahedron: Asymmetry 16 2005 1079 1084
17. R.A. Abramovitch, M. Saha, E.M. Smith, and R.T. Coutts J. Am. Chem. Soc. 89 1967 1537
18. K. Wiederholt, and L.W. McLaughlin Nucleic Acids Res. 27 1999 2487 2493
19. Considering the weak solubility of (±)-3, an attempt at resolution was tried by resorting to alcoholysis of the corresponding diacetyl derivative (±)-5 obtained by conventional acetylation with pyridine/acetic anhydride of 3,3′-dihydroxymethyl-2,2′-bipyridine and successive N-oxidation by m-CPBA. Both the lipase from P. cepacia and M. miehei were able to catalyse the alcoholysis with n-butanol in t-BME, but a poor enantioselectivity was observed and consequently this approach was not considered further.
20. C.-S. Chen, and C.J. Sih Angew. Chem., Int. Ed. Engl. 28 1989 695 707
21. J.R. Bowers, G.W. Hopkins, G.P.A. Yap, and K.A. Wheeler Cryst. Growth Des. 5 2005 727 736
22. P.W. Baures, A. Wiznycia, and A.M. Beatty Bioorg. Med. Chem. 8 2000 1599 1605
23. R (aR)-(+)-5 28.7. Due to an anomalous chromatographic behaviour, the accurate determination of the ee of monoester 4 was not possible since the more retained enantiomer was eluted as an asymmetric very broad peak.