An efficient kinetic resolution of racemic betti base based on an enantioselective N,O-deketalization

Journal of Organic Chemistry

Volumn 70, Issue 21, 2005, Pages 8617-8620

  Dong, Yanmei ^a   Li, Rui ^a   Lu, Jun ^a   Xu, Xuenong ^a   Wang, Xinyan ^a   Hu, Yuefei ^a  

^a TSINGHUA UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

REACTION KINETICS; SALTS;

ENANTIOMERS; ENANTIOSELECTIVE N,O-DEKETALIZATION; L-(+)- TARTARIC ACIDS; RACEMIC BETTI BASE;

ORGANIC ACIDS;

ACETAL; BASE; BETTI BASE; TARTARIC ACID; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; ASYMMETRIC SYNTHESIS; BENZYLATION; CHIRALITY; DERIVATIZATION; ENANTIOMER; ENANTIOSELECTIVITY; RACEMIC MIXTURE; STRUCTURE ANALYSIS;

EID: 26844474118     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051328j     Document Type: Article

References (26)

1. For selected reviews, see: (a) Soai, K.; Niwa, S. Chem. Rev. 1992, 92, 833-856.
2. (b) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835-875.
3. (c) Corey, E. J.; Helal, C. J. Angew. Chem., Int. Ed. 1998, 37, 1986-2012.
4. Pu, L.; Yu, H. B. Chem. Rev. 2001, 101, 757-824.
5. For selected reviews, see: (a) Husson, H.-P.; Royer, J. Chem. Soc. Rev. 1999, 28, 383-394.
6. (b) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
7. (a) Yamazaki, N.; Dokoshi, W.; Kibayashi, C. Org. Lett. 2001, 3, 193-196.
8. (b) Ito, T.; Yamazaki, N.; Kibayashi, C. Org. Lett. 2002, 4, 2469-2472.
9. For selected references, see: (a) Cardelliccnio, C.; Ciccarella, G.; Naso, F.; Schingaro, E.; Scordari, F. Tetrahedron: Asymmetry 1998, 9, 3667-3675.
10. (b) Cardellicchio, C.; Ciccarella, G.; Naso, F.; Perna, F.; Tortorella, P. Tetrahedron 1999, 55, 14685-14692.
11. (c) Palmieri, G. Tetrahedron: Asymmetry 2000, 11, 3361-3373.
12. (d) Liu, D.; Zhang, L.; Wang, Q.; Da, C.; Xin, Z.; Wang, R.; Choi, M. C. K.; Chan, A. S. C. Org. Lett. 2001, 3, 2733-2735.
13. (e) Cimarelli, C.; Mazzanti, A.; Palmieri, G.; Volpini, E. J. Org. Chem. 2001, 66, 4759-4765.
14. (f) Wang, Y.; Li, X.; Ding, K. Tetrahedron: Asymmetry 2002, 13, 1291-1297.
15. (g) Ji, J.; Qiu, L.; Yip, C. W.; Chan, A. S. C. J. Org. Chem. 2003, 68, 1589-1590.
16. (a) Lu, J.; Xu, X.; Wang, C.; He, J.; Hu, Y.; Hu, H. Tetrahedron Lett. 2002, 43, 8367-8369.
17. (b) Lu, J.; Xu, X.; Wang, S.; Wang, C.; Hu, Y.; Hu, H. J. Chem. Soc., Perkin Trans. 1 2002, 2900-2903.
18. (c) Xu, X.; Lu, J.; Li, R.; Ge, Z.; Dong, Y.; Hu, Y. Synlett 2004, 122-124.
19. (d) Xu, X.; Lu, J.; Dong, Y.; Li, R.; Ge, Z.; Hu, Y. Tetrahedron: Asymmetry 2004, 15, 475-479.
20. (e) Dong, Y.; Sun, J.; Wang, X.; Xu, X.; Cao, L.; Hu, Y. Tetrahedron: Asymmetry 2004, 15, 1667-1672.
21. (f) Wang, X.; Dong, Y.; Sun, J.; Xu, X.; Li, R.; Hu, Y. J. Org. Chem. 2005, 70, 1897-1900.
22. Betti, M. Organic Syntheses; Wiley & Sons: New York, 1941; Collect. Vol. 1, pp 381-383.
23. Betti, M. Gazz. Chim. Ital. 1907, 36, 392-395.
24. For selected reviews on kinetic resolution, see: (a) Kagan, H. B.; Fiaud, J. C. Top. Stereochem. 1988, 18, 249-330.
25. (b) Keith, J. M.; Larrow, J. F.; Jacobsen, E. N. Adv. Synth. Catal. 2001, 1, 5-26.
26. Szatmari, I.; Martinek, T. A.; Lazar, L.; Koch, A.; Kleinpeter, E.; Neuvonen, K.; Fulop, F. J. Org. Chem. 2004, 69, 3645-3653.