A P-chirogenic β-aminophosphine synthesis by diastereoselective reaction of the α-metallated PAMP-borane complex with benzaldimine

Tetrahedron Asymmetry

Volumn 15, Issue 13, 2004, Pages 2061-2065

  Camus, Jean Michel ^a   Andrieu, Jacques ^a   Richard, Philippe ^a   Poli, Rinaldo ^a,b   Darcel, Christophe ^a   Jugé, Sylvain ^a  

^a UNIVERSITÉ DE BOURGOGNE   (France)

^b LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZALDIMINE; BETA AMINOPHOSPHINE; BORANE DERIVATIVE; CHELATE; IMINE; LITHIUM ION; NITROGEN; PHOSPHINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; CHEMICAL REACTION; COMPLEX FORMATION; DIASTEREOISOMER; DISSOCIATION; EPIMERIZATION; HEATING; METALLATION; PHASE TRANSITION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 3142534623     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.05.031     Document Type: Article

References (52)

1. Gravilov K.N., Polosukhin A.I. Russ. Chem. Rev. 69:2000;661-682
2. Fache F., Schultz E., Tommasino L., Lemaire M. Chem. Rev. 100:2000;2159-2231
3. Braunstein P., Naud F. Angew. Chem., Int. Ed. 40:2001;680-699
4. For pertinent articles on the regioselective reaction of P, N chiral ligand complexes, see: Cross G., Vriesema B.K., Boven G., Kellogg R.M., van Bolhuis F. J. Organomet. Chem. 370:1989;357-381
5. Sawamura M., Ito Y. Chem. Rev. 92:1992;857-871
6. Lloyd-Jones G., Butts C.P. Tetrahedron. 1998;901-914
7. Helmchen G., Pfaltz A. Acc. Chem. Res. 33:2000;336-345
8. Anderson J.C., Cubbon R.J., Harling J.D. Tetrahedron: Asymmetry. 12:2001;923-935
9. For recent examples of multidendate ligands derived from chiral β-aminophosphines, see: Saitoh A., Uda T., Moritomo T. Tetrahedron: Asymmetry. 10:1999;4501-4511
10. Quirmbach M., Holtz J., Taranov V.I., Börner A. Tetrahedron. 56:2000;775-780
11. Bennett J., Rae A.D., Salem G., Ward N.C., Waring P., Wells K., Willis A.C. J. Chem. Soc., Dalton Trans. 2002;234-243
12. For representative examples of β-aminoalkyl phosphines, see: Horner L., Dickerhof K. Phosphorus Sulfur. 15:1983;331-349
13. Hayashi T., Konishi M., Fukushima M., Kanehira K., Hioki T., Kumada M. J. Org. Chem. 48:1983;2195-2202
14. Christoffers J. Helv. Chim. Acta. 81:1998;845-852
15. Andrieu J., Richard P., Camus J.-M., Poli R. Inorg. Chem. 41:2002;3876-3885
16. Malkov A.V., Hand J.B., Kocovsky P. J. Chem. Soc., Chem. Commun. 2003;1948-1949
17. For representative examples of chiral phosphines β-azacycles, see: Kanai M., Koga K., Tomioka K. Tetrahedron Lett. 33:1992;7193-7196
18. Sprinz J., Helmchen G. Tetrahedron Lett. 34:1993;1769-1772
19. Yang H., Alvarez M., Lugan N., Mathieu R. J. Chem. Soc., Chem. Commun. 1995;1721-1722
20. Pellet-Rostaing S., Saluzzo C., Ter Halle R., Breuzard J., Vial L., Le Guyader F., Lemaire M. Tetrahedron: Asymmetry. 12:2001;1983-1985
21. Stranne R., Vasse J.L., Moberg C. Org. Lett. 3:2001;2525-2528
22. Tao B., Fu G.C. Angew. Chem., Int. Ed. 41:2002;3892-3894
23. Mino T., Tanaka Y., Sakamoto M., Fujita T. Tetrahedron: Asymmetry. 12:2001;2435-2440
24. For representative examples of chiral β-imino phosphines, see: Saitoh A., Misawa M., Moritomo T. Synlett. 1999;483-485
25. Hiroi K., Watanabe K. Tetrahedron: Asymmetry. 12:2001;3067-3071
26. Barclay C.E., Deeble G., Doyle R.J., Elix S.A., Salem G., Jones T.L., Wild S.B., Willis A. J. Chem. Soc., Dalton Trans. 1995;57-65
27. Danjo H., Higuchi M., Yada M., Imamoto T. Tetrahedron Lett. 45:2004;603-606
28. Horner L., Simons G. Phosphorus Sulfur. 19:1984;77-89
29. Yang H., Lugan N., Mathieu R. Organometallics. 16:1997;2089-2095
30. Wolfe B., Livinghouse T. J. Am. Chem. Soc. 120:1998;5116-5117
31. Miura T., Yamada H., Kikuchi S.-I., Imamoto T. J. Org. Chem. 65:2000;1877-1880
32. Andrieu J., Steele B.R., Screttas C.G., Cardin C., Fornies J. Organometallics. 17:1998;839-845
33. Andrieu J., Camus J.-M., Dietz J., Richard P., Poli R. Inorg. Chem. 40:2001;1597-1605
34. Camus J.M., Andrieu J., Richard P., Poli R. Eur. J. Inorg. Chem. 2004;1081-1091
35. Moulin D., Bago S., Bauduin C., Darcel C., Jugé S. Tetrahedron: Asymmetry. 11:2000;3939-3956
36. For representative reactions of P-chirogenic carbanions with various electrophiles, see: Jugé S., Merdès R., Stéphan M., Genêt J.P. Phosphorus Sulfur. 77:1993;199
37. Muci A.R., Campos K.R., Evans D.A. J. Am. Chem. Soc. 117:1995;9075-9076
38. Zhu G., Terry M., Zhang X. Tetrahedron Lett. 37:1996;4475-4478
39. Nagata K., Matsukawa S., Imamoto T. J. Org. Chem. 65:2000;4185-4188
40. Sugama H., Saito H., Danjo H., Imamoto T. Synthesis. 15:2001;2348-2353
41. For the addition of secondary phosphine boranes to imines to give the corresponding α-aminophosphine derivatives, see: Ben-Aroya Bar-Nir B., Portnoy M. Tetrahedron Lett. 41:2000;6143-6147
42. Jugé S., Stéphan M., Laffitte J.A., Genêt J.P. Tetrahedron Lett. 31:1990;6357-6360
43. For pertinent reviews on the Wittig reaction and its mechanism, see: Maryanoff B.E., Reitz A.B. Chem. Rev. 89:1989;863-927
44. Mari F., Lahti P.M., McEwen W.E. J. Am. Chem. Soc. 114:1992;813-821
45. Brisset H., Gourdel Y., Pellon P., Le Corre M. Tetrahedron Lett. 34:1993;4523-4526
46. van Leeuwen P.W.N.M., Claver C. Rhodium Catalyzed Hydroformylation. Catalysis by Metal Complexes. Vol. 22:2000;Kluwer, Dordrecht
47. (a) Andrieu, J.; Camus, J.-M.; Richard, P.; Poli, R.; Gonsalvi, L.; Perruzzini, M., in preparation
48. Gladiali S., Dore A., Fabbri D., De Lucchi O., Manassero M. Tetrahedron: Asymmetry. 5:1994;511-514
49. Lagasse F., Kagan H.B. Chem. Pharm. Bull. 48:2000;315-324
50. Bigelow L.A., Eatough H. Organic Syntheses, 2nd ed. Coll. Vol. 1:1941;80-81 J. Wiley, New York
51. Crystallographic data for 6a has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 231951. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1 EZ, UK [fax: +44(0)-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk]
52. Masdeu A.M., Orejón A., Ruiz A., Castillón S., Claver C. J. Mol. Catal. A. 94:1994;149-156