Diastereoselectivity in nucleophilic displacement reactions at phosphorus; isolation and characterization of a pentacoordinated intermediate

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2217-2220

  Merckling, Franco Alberto ^a   Rüedi, Peter ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHORUS COMPOUND;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 17144461382     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00275-4     Document Type: Article

References (24)

1. (a) Merckling, F.A.; Rüedi, P. Chimia 1994, 48, 279.
2. (b) Merckling, F.A. PhD Thesis, University of Zurich 1993.
3. (a) Gorenstein, D.G.; Rowell, R. J. Am. Chem. Soc. 1979, 101, 4925-4928.
4. (b) Gorenstein, D.G.; Rowell, R.; Findlay, J. J. Am. Chem. Soc. 1980, 102, 5077-5081.
5. (c) Day, R.O.; Gorenstein, D.G.; Holmes, R.R. Inorg. Chem. 1983, 22, 2192-2195.
6. (d) Yang, J.-C; Shah, D.O.; Rao, N.U.M.; Freeman, W.A.; Sosnovsky, G.; Gorenstein, D.G. Tetrahedron 1988, 44, 6305-6314.
7. 5-phosphabicyclo[4.4.0]decan-3-ones and related ring systems see (a) Verkade, J.G. Phosphorus Sulfur 1976, 2, 251-281.
8. (b) Maryanoff, B.E.; Hutchins, R.O.; Maryanoff, C.A. Top. Stereochem. 1979, 11, 187-326.
9. p,NH = 11).
10. 1/2 = 37).
11. Wadsworth, W.S., Jr.; Larsen, S.; Horten, H.L. J. Org. Chem. 1973, 38, 256-263.
12. +).
13. 13C-NMR-Spektroskopie, G. Thieme Verlag: Stuttgart, New York; 1984, pp. 162-170.
14. Hohnes, R.R. Pentacoordinated Phosphorus, ACS Monograph 176; American Chemical Society, Washington D.C. 1980, Vol. 2; pp. 188-227.
15. (a) For a comprehensive, critical review covering the last 4 decades of research on that subject see: Thatcher, G.R.J.; Kluger, R. Advances in Physical Organic Chemistry 1989, 25, 99-265.
16. See also (b) Hall, C.R.; Inch, T.D. Tetrahedron 1980, 36, 2059-2095.
17. For actual investigations concerning catalysed versus uncatalysed nucleophilic reactions at phosphorus see (a) Corriu, R.J.P.; Lanneau, G.F.; Leclercq, D. Tetrahedron 1986, 42, 5591-5600.
18. (b) ibid. 1989, 45, 1959-1974.
19. (a) Ramirez, F.; Marecek, J.F, Okazaki, H. J. Amer. Chem. Soc. 1976, 98, 5310-5319.
20. (b) Ramirez, F.; Marecek, J.F. Tetrahedron Lett. 1976, 3791-3794.
21. (c) ibid. 1977, 967-970.
22. (d) Pure Appl. Chem. 1980, 52, 1021-1045.
23. (e) Ramirez, F.; Marecek, J.F.; Tsuboi, H.; Okazaki, H. J. Org. Chem. 1977, 42, 771-778.
24. 1H, TMS = 0).