An efficient optical resolution of nitrogen-centered chiral β-hydroxy-tetraalkylammonium salts via complexation with (R)-BINOL

Tetrahedron Letters

Volumn 48, Issue 24, 2007, Pages 4183-4185

  Tayama, Eiji ^a   Tanaka, Hiroyuki ^a  

^a NIIGATA UNIVERSITY   (Japan)

Author keywords

Ammonium salts; Complexation; Diastereoselectivity; Nitrogen; Optical resolution

Indexed keywords

AMMONIUM DERIVATIVE; BROMIDE; NITROGEN; SODIUM CHLORIDE;

ARTICLE; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; OPTICAL RESOLUTION;

EID: 34248548668     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.078     Document Type: Article

References (23)

1. Pope W.J., and Peachey S.J. J. Chem. Soc. (1899) 1127-1131
2. Recently, the absolute configuration was determined by a single crystal X-ray diffraction, see:. Torbeev V.Y., Lyssenko K.A., Kharybin O.N., Antipin M.Y., and Kostyanovsky R.G. J. Phys. Chem. B 107 (2003) 13523-13531
3. Toda F., Mori K., Stein Z., and Goldberg I. Tetrahedron Lett. 30 (1989) 1841-1844
4. Meisenheimer J., Glawe H., Greeske H., Schorning A., and Vieweg E. Liebig Ann. Chemie. 449 (1926) 188-213
5. Meisenheimer J. Chem. Ber. 41 (1908) 3966-3976
6. Tayama E., Nanbara S., and Nakai T. Chem. Lett. 35 (2006) 478-479
7. Shimomoto, A.; Yonezawa, H.; Takizawa, S.; Sasai, H. Jpn. Kokai Tokkyo Koho JP 2006076911 A 20060323, 2006.
8. Glaeske K.W., and West F.G. Org. Lett. 1 (1999) 31-33
9. Previous papers have shown that BINOL and some of quaternary ammonium salts form 1:1 complexes. These studies were applied for optical resolution of rac-BINOL, see:. Ha W., and Shan Z. Tetrahedron: Asymmetry 17 (2006) 854-859
10. Toda F., Yoshizawa K., Hyoda S., Toyota S., Chatziefthimiou S., and Mavridis I.M. Org. Biomol. Chem. 2 (2004) 449-451
11. Wang Y., Sun J., and Ding K. Tetrahedron 56 (2000) 4447-4451
12. Toda F., Tanaka K., Stein Z., and Goldberg I. J. Org. Chem. 59 (1994) 5748-5751
13. Tanaka K., Okada T., and Toda F. Angew Chem. Int. Ed. Engl. 32 (1993) 1147-1148
14. 4, THF, 0 °C to rt; (iii) allyl bromide, rt]. For more details, see the Supplementary data.
15. Use of ethanol as solvent provided the comparable result.
16. 3) did not show any diastereomerically separated peaks.
17. Compound 1a was stable for several days in a freezer without racemization.
18. The specific analysis condition (eluent system) of 1a was found by the analysis request to Daicel Chemical Industries, Ltd CPI Company, Chiral Separation Service.
19. Further optical resolution of (S)-1a (82% ee) with (R)-BINOL (0.85 equiv) in dichloromethane improved the enantio-purity to 93-95% ee. After one more optical resolution of the resolved (S)-1a, the enantio-purity was improved to >95% ee (determined by HPLC analysis).
20. CCDC-640938 contains the supplementary crystallographic data for this Letter. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
21. Use of a chloride salt as substrate provided the corresponding 1:1 complex with the similar yield and selectivity, but an iodide salt did not.
22. By our preliminary studies, it was found that a β-hydroxy group of ammonium salt is necessary for complexation with BINOL.
23. 25 -5.2 (c 1.00, EtOH). For more details, see the Supplementary data.