Phosphitylation via the Mitsunobu reaction

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 1087-1090

  Grice, I Darren ^a   Harvey, Peta J ^a   Jenkins, Ian D ^a   Gallagher, Michael J ^b   Ranasinghe, Millagahamada G ^b  

^a GRIFFITH UNIVERSITY   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINIC ACID DERIVATIVE; PHOSPHITE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030032948     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02282-1     Document Type: Article

References (23)

1. Mitsunobu, O. Synthesis 1981, 1-28.
2. Hughes, D.L. Organics Reactions 1992, 42, 335-656.
3. Mitsunobu, O. ; Jenkins, I.D. Encyclopedia of Reagents for Organic Synthesis ; ed. L. A Paquette, Wiley, Chichester, 1995.
4. Mitsunobu, O. ; Eguchi, M. ; Bull. Chem. Soc.Jap. 1971, 44, 3427-3430 ; Kay, P.B. ; Trippett, S. J.Chem. Soc. Perkin Trans 1, 1987, 1813-1815.
5. Mitsunobu, O. ; Eguchi, M. ; Bull. Chem. Soc.Jap. 1971, 44, 3427-3430 ; Kay, P.B. ; Trippett, S. J.Chem. Soc. Perkin Trans 1, 1987, 1813-1815.
6. Sim, M.M, ; Kondo, H.; Wong, C-H. J.A.m.Chem.Soc. 1993, 115, 2260-2267.
7. Caruthers, M.H. Science 1985, 230, 281-285.
8. Trost, B.M (ed.) Comprehensive Organic Synthesis ; Vol 6, Pergamon, Oxford, 1991 ; p 616.
9. Perich, J.W. ; Johns, R.B. Tetrahedron lett. 1987, 28, 101-102.
10. Perich, J.W. ; Johns, R.B. Synthesis 1988, 142-144.
11. Harvey, P. ; Jenkins, I. D. Tetrahedron Lett. 1994, 35, 9775-9778.
12. Camp, D. ; Jenkins, I.D. Aust. J. Chem. 1992, 45, 47-55.
13. Camp, D. ; Jenkins, I.D. J. Org. Chem. 1989, 54, 3045-3054.
14. Von Itzstein, M. ; Jenkins, I.D. J.Chem. Soc Perkin Trans, 1 1987, 2057-2060 ; 1986, 437-445.
15. Von Itzstein, M. ; Jenkins, I.D. J.Chem. Soc Perkin Trans, 1 1987, 2057-2060 ; 1986, 437-445.
16. Von Itzstein, M. ; Jenkins, I.D. Aust. J. Chem. 1984, 37, 2447-2451; 1983, 36, 557-563.
17. Von Itzstein, M. ; Jenkins, I.D. Aust. J. Chem. 1984, 37, 2447-2451; 1983, 36, 557-563.
18. For reasons that are not yet clear, two equivalents of betaine appeared to be required. When equimolar amounts of betaine 1 and dimethyl phosphite were employed, substantial amounts of unreacted dimethyl phosphite, δ10.0 ppm, remained.
19. Tebby, J.C. Handbook of Phosphorus -31 NMR Data ; CRC Press ; Boca Raton, 1991
20. 31P nmr and is based on integration of the phosphite product peak relative to the intermediate peaks δ 129-140.
21. Dimethyl phenyl phosphite was also formed cleanly by changing the order of addition, i.e. addition of dimethyl phosphite to pre-formed diphenoxytriphenylphosphorane.
22. Isopropyl "hypophosphite" was prepared from hypophosphorous acid and isopropyl alcohol by azeotropic removal of water with benzene (M.J. Gallager, M.G. Ranasinghe and I.D. Jenkins, J. Org. Chem., submitted)
23. Centofanti, L.F. Inorg. Chem. 1973, 12, 1131-1133.