1-(a-Aminobenzyl)-2-naphthol: A new chiral auxiliary for the synthesis of enantiopure a-aminophosphonic acids

Chemistry - A European Journal

Volumn 15, Issue 27, 2009, Pages 6718-6722

  Metlushka, Kirill E ^a,b   Kashemirov, Boris A ^b   Zheltukhin, Viktor F ^a   Sadkova, Dilyara N ^a   Büchner, Bernd ^c   Hess, Christian ^c   Kataeva, Olga N ^a,c   McKenna, Charles E ^b   Alfonsov, Vladimir A ^a  

^a A E ARBUZOV INSTITUTE OF ORGANIC AND PHYSICAL CHEMISTRY   (Russian Federation)

^b UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

^c IFW DRESDEN   (Germany)

Author keywords

Asymmetric synthesis; Betti bases; Chiral auxiliaries; Imines

Indexed keywords

2-NAPHTHOL; AMINOPHOSPHONATES; ASYMMETRIC SYNTHESIS; BETTI BASES; CHIRAL AUXILIARIES; CHIRAL CENTERS; DIASTEREO-SELECTIVITY; DIASTEREOMER; DIASTEREOMERS; DIASTEREOSELECTIVE SYNTHESIS; ENANTIOPURE; IMINES; ROOM TEMPERATURE; SINGLE CRYSTAL X-RAY STRUCTURES; TRIFLUOROACETIC ACIDS;

ACIDS; CRYSTAL STRUCTURE; ELECTRON TRANSITIONS; PHENOLS; TOLUENE;

NITROGEN COMPOUNDS;

EID: 67649662479     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200802540     Document Type: Article

References (45)

1. a) F. R. Atherton, C. H. Hassal, R. W. Lambert, J. Med. Chem. 1986, 29, 29-40;
2. b) M. C. Allen, W. Fuhrer, B. Tuck, R. Wade, J. M. Wood, J. Med. Chem. 1989, 32, 1652-1661;
3. c) P. Kafarski, B. Lejczak, Phosphorus Sulfur Silicon Relat. Eiern. 1991, 63, 193-215;
4. d) Aminophosphonic and Aminophosphinic Acids (Eds.: V. P. Kukhar, H. R. Hudson), Wiley, New York, 2000, pp. 1-634;
5. e) J. Grembecka, A. Mucha, T. Cierpicki, P. Kafarski, J. Med Chem. 2003, 46, 2641-2655;
6. f) M. Drag, J. Grembecka, M. Pawelczak, P. Kafarski, Eur. J. Med. Chem. 2005, 40, 764-771;
7. g) A. Biasone, P. Tortorella, C. Campestre, M. Agamennone, S. Preziuso, M. Chiappini, E. Nuti, P. Carelli, A. Rosselo, F. Mazza, C. Gallina, Bioorg. Med. Chem. 2007, 15, 791-799;
8. h) E. D. Naydenova, P. T. Todorov, N. Topashka-Ancheva, G. T. Momekov, T. Z. Yordanova, S. M. Konstantinov, K. D. Troev, Eur. J. Med. Chem. 2008, 43, 1199-1205.
9. a)J. Uziel, J. P. Genet, Russ. J. Org. Chem. 1997, 33, 1521-1542;
10. b)R. A. Cherkasov, V. I. Galkin, Russ. Chem. Rev. 1998, 67, 857882.
11. a) E. Kuliszewska, M. Hanbauer, F. Hammerschmidt, Chem. Eur. J. 2008, 14, 8603-8614;
12. b) V. Coeffard, I. Beaudet, M. Evain, E. Le Grognec, J.-P. Quintard, Eur. J. Org. Chem. 2008, 3344-3351.
13. c) For a review, see: M. Ordóñez, H. Rojas-Cabrera, C. Cativiela, Tetrahedron 2009, 65, 17-49.
14. a) Y. Wang, F. Wang, Y. Wang, Z. Miao, R. Chen, Adv. Synth. Catal. 2008, 350, 2339-2344;
15. b) G. M. Gilmore, H. A. McBride, J. Am. Chem. Soc. 1972, 94, 4361;
16. c) C. Yuan, S. Cui, Phosphorus Sulfur Silicon Relat. Elem. 1991, 55, 159-164;
17. d) K. M. Yager, C. M. Taylor, A. B. Smith, J. Am. Chem. Soc. 1994, 116, 9377-9378;
18. e) I. M. Lefebvre, S. A. Evans, J. Org. Chem. 1997, 62, 7532-7533;
19. f) M. Mikolajczyk, P. Lyzwa, J. Drabowicz, Tetrahedron: Asymmetry 1997, 8, 3991-3994;
20. g) F. A. Davis, S. Lee, H. Yan, D. D. Titus, Org. Lett. 2001, 3, 1757-1760.
21. a) O. I. Kolodiazhnyi, E. V. Grishkun, S. Sheiko, O. Demchuk, H. Thoennessen, P. G. Jones, R. Schmutzler, Tetrahedron: Asymmetry 1998, 9, 1645-1649;
22. b) G. A. Kachkovskii, N. V. Andrushko, S. Yu. Sheiko, 0.1. Kolodyazhnyi, Russ. J. Gen. Chem. 2005, 75, 17351743.
23. a) H. Sasai, S. Arai, Y. Tahara, M. Shibasaki, J. Org. Chem. 1995, 60, 6656-6657;
24. b) H. Gröger, Y. Saida, H. Sasai, K. Yamaguchi, J. Martens, M. Shibasaki, J. Am. Chem. Soc. 1998,120, 3089-3103;
25. c) G. D. JoIy, E. N. Jacobsen, J. Am. Chem. Soc. 2004, 126, 4102-4103;
26. d)T. Akiyama, H. Morita, J. Itoh, K. Fuchibe, Org. Lett. 2005, 7, 25832585;
27. e) D. Pettersen, M. Marcolini, L. Bernardi, F. Fini, R. P. Herrera, V. Sgazzani, A. Ricci, J. Org. Chem. 2006, 71, 6269-6272;
28. f) B. Saito, H. Egami, T. Katsuki, J. Am. Chem. Soc. 2007, 129, 19781986.
29. a) V. F. Zheltukhin, K. E. Metlushka, D. N. Sadkova, C. E. McKenna, B. A. Kashemirov, V. A. Alfonsov, Mendeleev Commun. 2007, 4, 239-240;
30. b) V. A. Alfonsov, K. E. Metlushka, C. E. McKenna, B. A. Kashemirov, O. N. Kataeva, V. F. Zheltukhin, D. N. Sadkova, A. B. Dobrynin, Synlett 2007, 0488-0490.
31. a) T. K. Gazizov, A.M. Kibardin, V. A. Kharlamov, A. A. Karelov, A. N. Pudovik, Zh. Obshch. Khim. 1977, 47, 2465-2468
32. [T. K. Gazizov, A. M. Kibardin, V. A. Kharlamov, A. A. Karelov, A. N. Pudovik, Chem. Abstr. 1978, 88, 89766g];
33. b)J. Consiglio, S. Bailla, P. Finocchiaro, Phosphorus Sulfur Silicon Relat. Elem. 1996,117, 37-54;
34. c) O. I. Kolodiazhnyi, Russ. Chem. Rev. 2006, 75, 227-253.
35. A. N. Pudovik, M. A. Pudovik, Zh. Obshch. Khim. 1969, 39, 16451646
36. [A. N. Pudovik, M. A. Pudovik, Chem. Abstr. 1969, 71, 91592z].
37. a) M. M. Sidky, F. M. Soliman, R. Shabana, Tetrahedron 1971, 27, 3431-3436;
38. b) F. Taran, E. Doris, J.-P. Noel, J. Labelled Compd. 2000, 43, 287-296.
39. E. Van Meenen, K. Moonen, A. Verwes, C. V. Stevens, J. Org. Chem. 2006,71, 7903-7906.
40. Elucidation of Structures by Physical and Chemical Methods, Vol. 11, Parti (Eds.: A. Weissberger, K.F. Bentley), Wiley Interscience, New York, 1963, pp. 378-409.
41. a) I. Szatmári, T. A. Martinek, L. Lázár, E. Fülöp, Tetrahedron 2003, 59, 2877-2884;
42. b) I. Szatmári, T. A. Martinek, L. Lázár, A. Koch, E. Kleinpeter, K. Neuvonen, F. Fülöp, J. Org. Chem. 2004, 69, 36453653.
43. H. E. Smith, N. E. Cooper, J. Org. Chem. 1970, 35, 2212-2215.
44. C. Cardellicchio, G. Ciccarella, F. Naso, E. Schingaro, F. Scordari, Tetrahedron: Asymmetry 1998, 9, 3667-3675.
45. L. Berlicki, E. Rudzinska, P. Kafarski, Tetrahedron: Asymmetry 2003,74,1535-1539.