Sigmatropic [2,3]-Wittig rearrangement of α-allylic-heterosubstituted methylphosphonates. Part 21 : Rearrangement in the nitrogen series

Tetrahedron

Volumn 52, Issue 6, 1996, Pages 2075-2086

  Gulea Purcarescu, Mihaela ^a   About Jaudet, Elie ^a   Collignon, Noël ^a   Saquet, Monique ^b   Masson, Serge ^b  

^a IRCOF   (France)

^b UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030052033     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01045-9     Document Type: Article

References (31)

1. Part 1 : Gulea-Purcarescu, M.; About-Jaudet, E.; Collignon, N. J. Organometal. Chem. 1994, 464, C14-C16.
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4. Mikami, K.; Nakai, T. Synthesis, 1991, pp. 594-604.
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6. Brückner, R. Kontakte (Ed. française), 1993, pp. 3-14. ibid. 1994, pp. 2-14.
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13. This work is a part of the Thesis of M.G.-P., carried out in the framework of the "Réseau Interrégional de Recherche en Chimie Organique Fine Normande".
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21. Masson, S.; Saint-Clair, J. F.; Saquet, M. Synthesis, 1993, pp. 485-486.
22. Prepared in 87% yield (bp / 2 Torr = 110°C), according to Ref. 16.
23. 1, the diastereoselectivities of the rearrangement of the crotyl and of the cinnamyl derivatives were 0% and 90%, respectively.
24. Jackman, L. M.; Sternhell, S. Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry; Pergamon Press: Oxford, 1969; pp. 291-292.
25. 31p-Element Couplings : Phosphorus-Carbon Coupling. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G.; Quin, L. D. Eds.; VCH Publishers, Inc.: Deerfield Beach, 1987; pp. 409-410.
26. 31p-Element Couplings : Phosphorus-Carbon Coupling. In Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis; Verkade, J. G.; Quin, L. D. Eds.; VCH Publishers, Inc.: Deerfield Beach, 1987; pp. 409-410.
27. 1H NMR spectra.
28. Gulea-Purcarescu, M.; About-Jaudet, E.; Collignon, N. Tetrahedron Lett. 1995, 36, 6635-6638.
29. Pine, S. H. Org. React. 1970, 18, 403-464.
30. Schöllkopf, U.; Fellenberger, K.; Ritk, M. Liebigs Ann. Chem. 1970, 734, 106-115, and ref. cited therein.
31. Prepared in 61% yield (bp / 0.5 Torr = 95°C), according to Zorgdrager, J.; Broekhof, N. L J. M.; Van der Gen, A. Recl. Trav. Chim. Pays Bas, 1989, 108, 441-444.