2-Alkenylphosphonates and PO-Ylids Derived Thereof in trans Selective Horner-Wittig Olefination Reactions

Synlett

Volumn 1996, Issue 12, 1996, Pages 1197-1198

  Liu, Rong Qiang ^a   Schlosser, Manfred ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001703472     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5701     Document Type: Article

References (19)

1. Schlosser, M.; Liu, R.-q.; Synlett 1996, 1195.
2. Downie, I.M.; Morris, G.; J. Chem. Soc. 1965, 5771-5771; see also : Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Ruston, S.; J. Chem. Soc., Perkin Trans. I 1976, 2386-2390; Santelli-Rouvier, C.; Synthesis 1988, 64-66.
3. Downie, I.M.; Morris, G.; J. Chem. Soc. 1965, 5771-5771; see also : Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Ruston, S.; J. Chem. Soc., Perkin Trans. I 1976, 2386-2390; Santelli-Rouvier, C.; Synthesis 1988, 64-66.
4. Downie, I.M.; Morris, G.; J. Chem. Soc. 1965, 5771-5771; see also : Lythgoe, B.; Moran, T.A.; Nambudiry, M.E.N.; Ruston, S.; J. Chem. Soc., Perkin Trans. I 1976, 2386-2390; Santelli-Rouvier, C.; Synthesis 1988, 64-66.
5. 9. - Further experimental details concerning the preparation of the phosphonates and the characterization of the olefination products will be published in a Feature Article to appear 1997 in Synthesis.
6. Collington, E.W.; Meyers, A.I.; J. Org. Chem. 1971, 36, 3044-3046.
7. Hatch, L.F.; Nesbitt, S.S.; J. Am. Chem. Soc. 1950, 72, 727-730.
8. Hafner, A.; von Philipsborn, W.; Salzer, A.; Helv. Chim. Acta 1986, 69, 1757-1767.
9. Ignatev, V.M.; Zeilinger, I.A.; Vorobev, B.I.; Zh. Obshch. Khim. 1969, 39, 2433-2438; Chem. Abstr. 1970, 72, 111571t.
10. Ignatev, V.M.; Zeilinger, I.A.; Vorobev, B.I.; Zh. Obshch. Khim. 1969, 39, 2433-2438; Chem. Abstr. 1970, 72, 111571t.
11. Sasse, K.; Houben-Weyl : Methoden der organischen Chemie (ed. : Müller, E.), Thieme, Stuttgart, 1963, 12/1, 446-453.
12. Kosolapoff, G.M.; Org. React. 1951, 6, 173-338; Sasse, K.; Houben-Weyl : Methoden der organischen Chemie (ed. : Müller, E.), Thieme, Stuttgart, 1963, 12/1, 433-446; Bhattacharya, A.K.; Thyagarajan, G.; Chem. Rev. 1981, 81, 415-430.
13. Kosolapoff, G.M.; Org. React. 1951, 6, 173-338; Sasse, K.; Houben-Weyl : Methoden der organischen Chemie (ed. : Müller, E.), Thieme, Stuttgart, 1963, 12/1, 433-446; Bhattacharya, A.K.; Thyagarajan, G.; Chem. Rev. 1981, 81, 415-430.
14. Kosolapoff, G.M.; Org. React. 1951, 6, 173-338; Sasse, K.; Houben-Weyl : Methoden der organischen Chemie (ed. : Müller, E.), Thieme, Stuttgart, 1963, 12/1, 433-446; Bhattacharya, A.K.; Thyagarajan, G.; Chem. Rev. 1981, 81, 415-430.
15. 6 and Moreno-Mañas, M.; Pleixats, R.; Synth. Commun. 1992, 22, 2219-2228; Al-Badri, About-Jaudet, E.; Collignon, N.; Tetrahedron Lett. 1995, 36, 393-396
16. 6 and Moreno-Mañas, M.; Pleixats, R.; Synth. Commun. 1992, 22, 2219-2228; Al-Badri, About-Jaudet, E.; Collignon, N.; Tetrahedron Lett. 1995, 36, 393-396
17. Standard conditions : The 2-alkenylphosphonate (25 mmol) and potassium tert-butoxide (40 mmol) are conjointly dissolved in tetrahydrofuran (40 mL). After keeping the pale yellow solution for 1 h at 25 °C, it is cooled to -75 °C. The aldehyde is added dropwise, in the course of 10 min., and the reaction mixture is allowed to reach slowly 25 °C. After 1 h, it is adsorbed on silica gel (25 mL). Elution with hexane from a column filled with more (75 mL) silica gel (a total of 100 mL) and evaporation of the solvent gives a colorless oil, the stereoisomeric composition of which is analyzed by gas chromatography (30 m, dimethylpolysiloxane rubber DB-1, 60 - 180 °C; 30 m, DB-FFAP [polyethylene glycol + nitroterephthalic acid], 100 - 200 °C). The diene is isolated by distillation under reduced pressure.
18. After completion of the present work we have realized that the yields of olefins are considerably improved when the sodium hydride employed is activated by treatment with lithium aluminumhydride (see : Hubbard, J.L.; Tetrahedron Lett. 1988, 29, 3197-3200; see also : Soderquist, J.A.; Rivera, I.; Tetrahedron Lett. 1988, 29, 3195-3196).
19. After completion of the present work we have realized that the yields of olefins are considerably improved when the sodium hydride employed is activated by treatment with lithium aluminumhydride (see : Hubbard, J.L.; Tetrahedron Lett. 1988, 29, 3197-3200; see also : Soderquist, J.A.; Rivera, I.; Tetrahedron Lett. 1988, 29, 3195-3196).