Enantioselective copper catalyzed diels-alder reaction using chiral quinoline-phosphine ligand

Tetrahedron Letters

Volumn 39, Issue 52, 1998, Pages 9663-9666

  Brunel, Jean Michel ^a   Del Campo, Beatriz ^a   Buono, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER; PHOSPHINE DERIVATIVE;

ALKYLATION; ARTICLE; CATALYSIS; CHIRALITY; COMPLEX FORMATION; DRUG SYNTHESIS; ENANTIOMER; LIGAND BINDING; REACTION ANALYSIS;

EID: 0032564578     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02210-2     Document Type: Article

References (26)

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25. (6) 1 was prepared by exchange reaction at 110°C in 20 mL of anhydrous toluene between 163 mg of tris(dimethylamino)phosphine (1 mmole) and 176 mg of (S)-(+)-2-anilinomethylpyrrolidine (1 mmole) for 2 hours, followed by subsequent addition of 136 mg of hydroxyquinoleine (1 mmole). Slow crystallization in toluene afforded ligand 1 in 92% chemical yield as a white solid stable to air and moisture. Similar procedure was used in order to prepare ligand 2 (34% yield) which was purified by distillation (bp 220°C/0.05 mbar).
26. 2 (Fluka) (0.071 mmol, 26 mg) is treated with ligand 1 (0.071 mmol, 25 mg) in dichloromethane (10 mL) at room temperature for 15 minutes under an argon atmosphere. The resulting stirred dark brown solution was cooled to -78°C and N-acyl-1,3-oxazolidine-2-one (0.71 mmol, 100 mg) and freshly distilled cyclopentadiene (3.55 mmol, 235 mg) were added. The solution was slowly warmed to 25°C and stirred overnight. The reaction mixture was concentrated in vacuo and the crude material purified by flash chromatography affording the endo adduct with 2S absolute configuration in 75% yield (endolexo = >98/2) and 99% ee. The ee was determined by HPLC analysis using a Daicel Chiralcel OD-H column with 10% i-PrOH in hexane for elution (0.5 mL/min ; retention times 37.8 min (S) and 41.2 min (R)).