Diastereoselective alkynylation of chiral phosphinoylimines: preparation of optically active propargylamines

Tetrahedron Letters

Volumn 51, Issue 4, 2010, Pages 645-648

  Benamer, Mounira ^a   Turcaud, Serge ^a   Royer, Jacques ^a  

^a UNIVERSITÉ PARIS DESCARTES   (France)

Author keywords

Aluminum acetylides; Aluminum reagents; Asymmetric induction; Chiral phosphinoylimine; Propargylamines asymmetric synthesis

Indexed keywords

ALUMINUM DERIVATIVE; IMINE; LITHIUM; MAGNESIUM DERIVATIVE; PHOSPHINE DERIVATIVE;

ALKYNYLATION; ARTICLE; CHIRALITY; DIASTEREOISOMER; OPTICAL ROTATION; STEREOCHEMISTRY;

EID: 72149118716     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.091     Document Type: Article

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45. C-P = 8.2 Hz).
46. D 8.3 (c 2.2, MeOH).
47. 15 (1.64 mmol) was added at 0 °C to N-phosphinoylimine 4a (0.411 mmol) in anhydrous toluene (2 mL). The reaction mixture was stirred at room temperature for 1 h. The reaction was quenched by the addition of 3 ml of a 2 M Rochelle salt solution and the reaction mixture was stirred for 15 min at rt. The aqueous layer was separated and extracted with ethyl acetate. The organic layers were mixed and washed successively with water and brine. After drying, the solvent was evaporated under reduced pressure, and the oily residue was purified by column chromatography on silica gel (ether/n-heptane 6/4) to leave 5 as a white solid (56%).
48. C-P = 2.7 Hz); 133.2; 133.7; 140.0.
49. D 45.2 (c 3.7, MeOH).
50. 3).
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