Base-dependent regio- and diastereoselective alkylation of chiral perhydro 1,3,2-oxazabenzophosphorinane-2-oxides derived from (-)-8-benzylamino menthol

Synlett

Volumn , Issue 7, 2004, Pages 1300-1302

  Pedrosa, Rafael ^a   Maestro, Alicia ^a   Pérez Encabo, Alfonso ^a   Raliegos, Rubén ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

2 oxo 1,3,2 oxazaphosphorinanes; Alkyl phosphonates; Alkylation; Asymmetric synthesis; Diastereoselective reactions

Indexed keywords

BENZYL DERIVATIVE; MENTHOL; NITROGEN; PHOSPHONIC ACID DERIVATIVE; PHOSPHORUS; PHOSPHORUS DERIVATIVE;

ALKYLATION; ARTICLE; BENZYLATION; CHEMICAL REACTION; PROTON TRANSPORT; STEREOCHEMISTRY; SYNTHESIS;

EID: 2942724611     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822914     Document Type: Article

References (28)

1. For recent reviews see: (a) Bennani, Y. L.; Hanessian, S. Chem. Soc. Rev. 1997, 97, 3161. (b) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279. (c) Molt, O.; Schrader, T. Synthesis 2002, 2633. (d) Ansell, J.; Wills, M. Chem. Soc. Rev. 2002, 31, 259.
2. For recent reviews see: (a) Bennani, Y. L.; Hanessian, S. Chem. Soc. Rev. 1997, 97, 3161. (b) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279. (c) Molt, O.; Schrader, T. Synthesis 2002, 2633. (d) Ansell, J.; Wills, M. Chem. Soc. Rev. 2002, 31, 259.
3. For recent reviews see: (a) Bennani, Y. L.; Hanessian, S. Chem. Soc. Rev. 1997, 97, 3161. (b) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279. (c) Molt, O.; Schrader, T. Synthesis 2002, 2633. (d) Ansell, J.; Wills, M. Chem. Soc. Rev. 2002, 31, 259.
4. For recent reviews see: (a) Bennani, Y. L.; Hanessian, S. Chem. Soc. Rev. 1997, 97, 3161. (b) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279. (c) Molt, O.; Schrader, T. Synthesis 2002, 2633. (d) Ansell, J.; Wills, M. Chem. Soc. Rev. 2002, 31, 259.
5. (a) Hanessian, S.; Delorme, D.; Beaudoins, S.; Le Blanc, Y. J. Am. Chem. Soc. 1984, 106, 5754.
6. (b) Hanessian, S.; Andreotti, D.; Gomtsyan, A. J. Am. Chem. Soc. 1995, 117, 10393.
7. (a) Denmark, S. E.; Marlin, J. E. J. Org. Chem. 1987, 52, 5742.
8. (b) Denmark, S. E.; Kim, J. H. Can. J. Chem. 2000, 78, 673; and references therein.
9. Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879.
10. Denmark, S. E.; Dorow, R. L. J. Org. Chem. 1990, 55, 5926.
11. Denmark, S. E.; Amburgey, J. J. Am. Chem. Soc. 1993, 115, 10386.
12. Afarinkia, K.; Jones, C. L.; Yu, H. W. Synlett 2003, 509.
13. (a) Pedrosa, R.; Andrés, C.; Nieto, J.; Pozo, S. J. Org. Chem. 2003, 68, 4923.
14. (b) Pedrosa, R.; Andrés, C.; Rosón, C. D.; Vicente, M. J. Org. Chem. 2003, 1852.
15. (c) Pedrosa, R.; Andrés, C.; Heras, L.; Nieto, J. Org. Lett. 2002, 4, 2513.
16. Denmark, S. E.; Kim, J. H. J. Org. Chem. 1995, 60, 7535.
17. Denmark, S. E.; Chen, C.-T. J. Org. Chem. 1994, 59, 2922.
18. (a) Viljanen, T.; Tähtinen, P.; Pihlaja, K.; Fülöp, J. J. Org. Chem. 1998, 63, 618.
19. (b) Bentrude, W. G.; Tomasz, J. Synthesis 1984, 27.
20. CCDC contain supplementary crystallographic data for compounds 1 (CCDC 233645), 2 (CCDC 233647), 4 (CCDC 233644), and 8 (CCDC 233646), respectively. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retreiving.html or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB12 1EZ, UK; fax: (internat.) +44(1223)336033; e-mail: deposit@ccdc.cam.ac.uk.
21. (a) Afarinkia, K.; Angell, R.; Jones, C. L.; Lowman, J. Tetrahedron Lett. 2001, 42, 743.
22. (b) Bentrude, W. G.; Setzer, W. N.; Sopchik, A. E.; Bajwa, G. S.; Burright, D. D.; Hutchinson, J. P. J. Am. Chem. Soc. 1986, 108, 6669.
23. 4), filtered and concentrated. The residue was purified by flash chromatography on silica gel and hexane-EtOAc (1:2)as eluent.
24. Bennani, Y. L.; Hanessian, S. Tetrahedron 1996, 52, 13837.
25. Afarinkia, K.; Jones, C. L.; Yu, H.-W. Synlett 2003, 509.
26. See for instance: (a) Iula, D. M.; Gawley, R. E. J. Org. Chem. 2000, 65, 6196. (b) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764.
27. See for instance: (a) Iula, D. M.; Gawley, R. E. J. Org. Chem. 2000, 65, 6196. (b) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764.
28. Kranz, M.; Denmark, S. E.; Swiss, K. A.; Wilson, S. R. J. Org. Chem. 1996, 65, 8551.