Stereoselective synthesis of acyclic amino alcohols via von braun ring opening of chiral piperidines

Organic Letters

Volumn 10, Issue 15, 2008, Pages 3255-3257

  McCall, W Stephen ^a   Grillo, Teresa Abad ^a   Comins, Daniel L ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BENZYL BROMIDE; BENZYL DERIVATIVE; CYANAMIDE; CYANOGEN BROMIDE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

AMINO ALCOHOLS; BENZYL COMPOUNDS; CYANAMIDE; CYANOGEN BROMIDE; CYCLIZATION; PIPERIDINES; STEREOISOMERISM;

EID: 49649091566     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801123x     Document Type: Article

References (31)

1. (a) De Oliveira, L. F.; Costa, V. E. U. Tetrahedron: Asymmetry 2004, 15, 2583.
2. For synthesis of 1,3-amino alcohols, see: (b) Raghavan, S.; Rajender, A.; Joseph, S. C.; Rasheed, M. A.; Kumar, K. R Tetrahedron: Asymmetry 2004, 15, 365, and references cited therein.
3. (a) Hu, X.; Fan, C.; Zhang, F.; Tu, Y. Q. Angew. Chem., Int. Ed. 2004, 43, 1702.
4. (b) Gais, H.; Loo, R.; Roder, D.; Das, P.; Raabe, G. Eur. J. Org. Chem. 2003, 1500.
5. Schlessinger, R. H.; Gillman, K. W. Tetrahedron Lett. 1996, 37, 1331.
6. (a) Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, C. J., Eds.; JAI Press, Inc.: Greenwich, CT, 1996; Vol. 2, p 251.
7. (b) Comins, D. L.; Joseph, S. P. In Comprehensive Heterocyclic Chemistry, 2nd ed.; McKillop, A., Ed.; Pergamon Press: Oxford, England, 1996; Vol. 5,p 37.
8. (c) Comins, D. L. J. Heterocycl. Chem. 1999, 36, 1491.
9. (d) Joseph, S. P.; Comins, D. L. Curr. Opin. Drug Discovery Dev. 2002, 5, 870.
10. (e) Kuethe, J. T.; Comins, D. L. J. Org. Chem. 2004, 69, 5219.
11. (f) Comins, D. L.; Sahn, J. J. Org. Lett. 2005, 7, 5227.
12. (g) Gotchev, D. B.; Comins, D. L. J. Org. Chem. 2006, 71, 9393.
13. (h) Comins, D. L.; Higuchi, K. Beil. J. Org. Chem. 2007, 3, No. 42.
14. For recent examples, see: (a) Hunt, K. W.; Grieco, P. A. Org. Lett. 2002, 4, 245.
15. (b) Ramachandran, P. V.; Prabhudas, B.; Chandra, J. S.; Reddy, M. V. R. J. Org. Chem. 2004, 69, 6294.
16. (a) von Braun, J. Chem. Ber. 1900, 33, 1438.
17. Review (b) Hageman, H. A. Org. React. 1953, 7, 198.
18. (a) Albright, J. D.; Goldman, L. J. Am. Chem. Soc. 1969, 91, 4317.
19. (b) Fodor, G.; Abidi, S.; Carpenter, T. C. J. Org. Chem. 1974, 39, 1507.
20. Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1986, 27, 4549.
21. Brown, J. D.; Foley, M. A.; Comins, D. L. J. Am. Chem. Soc. 1988, 110, 7445.
22. For examples, see (a) Demko, Z. P.; Sharpless, K. B. Org. Lett. 2001, 3, 4091.
23. (b) Nekrasov, D. D. Russ. J. Org. Chem. (Engl. Transl.) 2004, 40, 1387.
24. (c) Nekrasov, D. D. Chem. Heterocycl. Compd. 2004, 40, 1107.
25. Saito, S.; Nakajima, H.; Inaba, M.; Moriwake, T. Tetrahedron Lett. 1989, 30, 87.
26. Casy, A. F.; Hassan, M. M. A. Tetrahedron 1967, 23, 2075.
27. (a) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
28. (b) Comins, D. L.; LaMunyon, D. H. Tetrahedron Lett. 1994, 35, 7343.
29. (c) Comins, D. L.; Guerra-Weltzien, L. Tetrahedron Lett. 1996, 37, 3807.
30. (d) Waldmann, H. Synthesis 1994, 535.
31. Comins, D. L.; O'Connor, S.; Al-awar, R. S. In Comprehensive Heterocyclic Chemistry III; Black, D., Ed.; Elsevier Ltd: Oxford, England, 2008; Vol. 7, p 41.