Regio- and stereoselective reductive opening of diene-ester derived monoepoxides with palladium catalyst and dimethylamine-borane complex

Tetrahedron Letters

Volumn 41, Issue 18, 2000, Pages 3335-3338

  David, Hervé ^a   Dupuis, Laurent ^a   Guillerez, Marie George ^a   Guibé, François ^a  

^a Laboratoire de Catalyse Moléculaire   (France)

Author keywords

Amine borane complexes; Epoxide hydrogenolysis; Palladium catalysis

Indexed keywords

ALCOHOL; ALKADIENE; BORANE DERIVATIVE; DIMETHYLAMINE; EPOXIDE; ESTER; FORMIC ACID; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY;

EID: 0034728941     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00380-4     Document Type: Article

References (12)

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3. Review on palladium-catalysed hydrogenolysis of allylic and propargylic compounds: Tsuji, J.; Mandai, T. Synthesis 1996, 1-24.
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6. Gomez-Martinez, P.; Dessolin, M.; Guibé, F.; Albericio, F. J. Chem. Soc., Perkin Trans. 1 1999, 2871-2874.
7. Hutchins, R. O.; Learn, K.; Fulton, R. P. Tetrahedron Lett. 1980, 21, 27-30.
8. 3J=7.5 Hz, 1H, vinylic H); 5.17 (s, 2H); 3.19-3.15 (broad m, 2H); 1.78 (broad s, 3H).
9. 4 and 0.385 g (1.1 equiv.) of dimethylamine-borane complex and the reaction mixture was stirred at room temperature for 15 min. The solvent was evaporated and the residue was directly purified by column chromatography to give 1.67 g (95%) of pure homoallylic alcohol 6.
10. 3J=7 Hz, 3H).
11. 3 was used as the hydride donor.
12. See for example: Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395-422.