Direct monoalkylation of alkyl phosphinates to access H-phosphinic acid esters

Synthesis

Volumn , Issue 2, 2006, Pages 325-331

  Abrunhosa Thomas, Isabelle ^a   Ribière, Patrice ^a   Adcock, Alicia C ^a   Montchamp, Jean Luc ^a  

^a TEXAS CHRISTIAN UNIVERSITY   (United States)

Author keywords

Alkylation; H phosphinic acid; Hypophosphite; Phosphinates; Phosphorus

Indexed keywords

ALKYLATION; BROMINE COMPOUNDS; ESTERS; LITHIUM; ORGANIC ACIDS; PHOSPHORUS;

H-PHOSPHOINIC ACID; HYPOPHOSPHITE; PHOSPHINATES;

PHOSPHORUS COMPOUNDS;

ALKYL GROUP; ALLYL COMPOUND; BROMIDE; BUTYLLITHIUM; ESTER DERIVATIVE; IODIDE; PHOSPHINE DERIVATIVE; PHOSPHINIC ACID DERIVATIVE; SILICATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ESTERIFICATION; QUANTUM YIELD; REACTION ANALYSIS; ROOM TEMPERATURE; TECHNIQUE; WARMING;

EID: 31544454737     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-924768     Document Type: Article

References (54)

1. Gallagher, M. J.; Ranasinghe, M. G.; Jenkins, I. D. Phosphorus, Sulfur Silicon Relat. Elem. 1996, 115, 255.
2. (a) Gallagher, M. J.; Sussman, J. Phosphorus 1975, 5, 91.
3. (b) Maier, L. Helv. Chim. Acta 1973, 56, 489.
4. (c) Wroblewski, A. E.; Verkade, J. G. J. Am. Chem. Soc. 1996, 118, 10168.
5. (d) See also reference 6.
6. (a) Fookes, C. J. R.; Gallagher, M. J. J. Chem. Soc., Perkin Trans. 1 1975, 1876.
7. (b) Fookes, C. J. R.; Gallagher, M. J.; Honneger, H. J. Chem. Soc., Chem. Commun. 1978, 324.
8. Nifant'ev, E. E.; Levitan, L. P. J. Gen. Chem. USSR (Engl. Transl.) 1965, 35, 762.
9. (a) Dingwall, J. G.; Ehrenfreund, J.; Hall, R. G.; Jack, J. Phosphorus Sulfur Relat. Elem. 1987, 30, 571.
10. (b) McCleery, P. P.; Tuck, B. J. Chem. Soc., Perkin Trans. 1 1989, 1319.
11. (c) Dingwall, J. G.; Ehrenfreund, J.; Hall, R. G. Tetrahedron 1989, 45, 3787.
12. (d) Baylis, E. K. Tetrahedron Lett. 1995, 36, 9385.
13. (e) Baylis, E. K. Tetrahedron Lett. 1995, 36, 9389.
14. (f) Froestl, W.; Mickel, S. J.; Hall, R. G.; von Sprecher, G.; Diel, P. J.; Strub, D.; Baumann, P. A.; Brugger, F.; Gentsch, C.; Jaekel, J.; Olpe, H.-R.; Rihs, G.; Vassout, A.; Waldmeier, P. C.; Bittiger, H. J. Med. Chem. 1995, 38, 3297.
15. (g) Bennett, S. N. L.; Hall, R. G. J. Chem. Soc., Perkin Trans. 1 1995, 1145.
16. Deprèle, S.; Montchamp, J.-L. J. Organomet. Chem. 2002, 643-644, 154.
17. For example: Ribière, P.; Bravo-Altamirano, K.; Antczak, M.; Hawkins, J. D.; Montchamp, J.-L. J. Org. Chem. 2005, 70, 4064.
18. The purification of H-phosphinate esters is often complicated by the very polar nature of these compounds, and their relative ease of hydrolysis. Benzyl alkyl-H-phosphinate esters are more labile than other alkyl esters.
19. (a) Deprèle, S.; Montchamp, J.-L. J. Org. Chem. 2001, 66, 6745.
20. (b) Deprèle, S.; Montchamp, J.-L. J. Am. Chem. Soc. 2002, 124, 9386.
21. Bravo-Altamirano, K.; Huang, Z.; Montchamp, J.-L. Tetrahedron 2005, 61, 6315.
22. See for example: (a) Nifant'ev, E. E.; Magdeeva, R. K.; Shchepet'eva, N. P. J. Gen. Chem. USSR (Engl. Transl.) 1980, 50, 1416.
23. (b) Karanewsky, D. S.; Badia, M. C.; Cushman, D. W.; DeForrest, J. M.; Dejneka, T.; Loots, M. J.; Perri, M. G.; Petrillo, E. W. Jr.; Powell, J. R. J. Med. Chem. 1988, 31, 204.
24. (c) Kabachnik, M. I.; Tsvetkov, E. N.; Chang, C.-Y. Dokl. Chem. (Engl. Transl.) 1959, 125, 309.
25. 3P(O)(OEt)H, 81%]: Kehler, J.; Ebert, B.; Dahl, O.; Krogsgaard-Larsen, P. Tetrahedron 1999, 55, 771.
26. 3P(O)(OEt)H, 88%]: Renard, P.-Y.; Vayron, P.; Taran, F.; Miokowski, C. Tetrahedron Lett. 1999, 40, 281.
27. 3P(O)(OAr)H, 32-75%]: Barabanov, V. I.; Abramov, V. S. J. Gen. Chem. USSR (Engl. Transl.) 1965, 35, 2215.
28. 3P(O)(OAlk)H, 60-75%]: Gruzdev, V. G.; Karavanov, K. V.; Ivin, S. V. J. Gen. Chem. USSR (Engl. Transl.) 1968, 38, 1499.
29. 3P(O)(OBu)H, 68%]: Gladshtein, B. M.; Shitov, L. N. J. Gen. Chem. USSR (Engl. Transl.) 1969, 39, 1913.
30. (f) Murata, Y.; Woodward, R. M.; Miledi, R.; Overman, L. E. Bioorg. Med. Chem. Lett. 1996, 6, 2073.
31. Kehler, J.; Ebert, B.; Dahl, O.; Krogsgaard-Larsen, P. J. Chem. Soc., Perkin Trans. 1 1998, 3241.
32. We thank Jakob Heid, Klemens Kaupmann, and Wolfgang Froestl (Novartis Pharma) for conducting the GTPgammaS binding assay.
33. Boyd, E. A.; Regan, A. C.; James, K. Tetrahedron Lett. 1994, 35, 4223.
34. (a) Bujard, M.; Gouverneur, V.; Mioskowski, C. J. Org. Chem. 1999, 64, 2119.
35. (b) Briot, A.; Bujard, M.; Gouverneur, V.; Nolan, S. P.; Mioskowski, C. Org. Lett. 2000, 2, 1517.
36. (a) Patel, D. V.; Gordon, E. M.; Schmidt, R. J.; Weller, H. N.; Young, M. G.; Zahler, R.; Barbacid, M.; Carboni, J. M.; Gullo-Brown, J. L.; Hunihan, L.; Ricca, C.; Robinson, S.; Seizinger, B. R.; Tuomari, A. V.; Manne, V. J. Med. Chem. 1996, 38, 435.
37. (b) Valentijn, A. R. P. M.; van den Berg, O.; van der Marel, G. A.; Cohen, L. H.; van Boom, J. H. Recl. Trav. Chim. Pays-Bas 1994, 113, 563.
38. For the conversion of RP(O)(OR′)H into RP(O)(OR′)C1 and esterification, see for example: (a) Bartlett, P. A.; Giangiordano, M. A. J. Org. Chem. 1996, 61, 3433.
39. (b) Mucha, A.; Kafarski, P.; Plenat, P.; Cristau, H.-J. Tetrahedron 1994, 50, 12743.
40. 31P NMR), though there too ion-pairs are possible]: (a) Galkin, V. I.; Khabibullina, A. B.; Smirnov, V. N.; Cherkasov, R. A.; Pudovik, A. N. Dokl. Chem. (Engl. Transl.) 1987, 292, 21.
41. (b) Moedritzer, K. J. Inorg. Nucl. Chem. 1961, 22, 19.
42. P-H = 203 Hz)]: Centofanti, L. F. Inorg. Chem. 1973, 12, 1131.
43. P-H = 200 Hz)]: Lutsenko, I. F.; Proskurnina, M. V.; Borisenko, A. A. Dokl. Chem. (Engl. Transl.) 1970, 193, 553.
44. P-H = 198 Hz)]: Stec, W.; Uznanski, B.; Houalla, D.; Wolf, R. C. R. Acad. Sci. Ser. C 1975, 281, 727.
45. P-H = 176 Hz)]: Livantsov, M. V.; Prishchenko, A. A.; Lutsenko, I. F. J. Gen. Chem. USSR (Engl. Transl.) 1986, 56, 1976.
46. (g) ROP(OR′)H has been proposed as a likely intermediate in the transesterification of alkyl phosphinates but could not be detected: Gallagher, M. J.; Honneger, H. J. Chem. Soc., Chem. Commun. 1978, 54.
47. Review: Montchamp, J.-L. J. Organomet. Chem. 2005, 690, 2388.
48. (a) Montchamp, J.-L.; Dumond, Y. R. J. Am. Chem. Soc. 2001, 123, 510.
49. (b) Anilinium hypophosphite is now also commercially available from Aldrich.
50. Froestl, W.; Mickel, S. J.; von Sprecher, G.; Diel, P. J.; Hall, R. G.; Maier, L.; Strub, D.; Melillo, V.; Baumann, P. A.; Bernasconi, R.; Gentsch, C.; Hauser, K.; Jaekel, J.; Karlsson, G.; Klebs, K.; Maitre, L.; Marescaux, C.; Pozza, M. F.; Schmutz, M.; Steinmann, M. W.; van Riezen, H.; Vassout, A.; Mondadori, C.; Olpe, H.-R.; Waldmeier, P. C.; Bittiger, H. J. Med. Chem. 1995, 38, 3313.
51. (a) Yamagishi, T.; Kusano, T.; Yokomatsu, T.; Shibuya, S. Synlett 2002, 1471.
52. (b) Yamagishi, T.; Kusano, T.; Kaboudin, B.; Yokomatsu, T.; Sakuma, C.; Shibuya, S. Tetrahedron 2003, 59, 767.
53. Petnehazy, I.; Jaszay, Z. M.; Szabo, A.; Everaert, K. Synth. Commun. 2003, 33, 1665.
54. Kabachnik, M. I.; Chang, J.-Y.; Tsvetkov, E. N. J. Gen. Chem. USSR (Engl. Transl.) 1962, 32, 3351.