Enantioselective reduction of ketones by borane catalysed by oxazaphospholidine oxides

Tetrahedron Letters

Volumn 37, Issue 1, 1996, Pages 39-42

  Chiodi, Olivier ^a   Fotiadu, Frédéric ^a   Sylvestre, Maud ^a   Buono, Gérard ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; PHENETHYL ALCOHOL;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; REDUCTION;

EID: 0030027143     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02078-0     Document Type: Article

References (20)

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16. Compound 6 can alternatively be obtained according to Koizumi's method : (S)-prolinol reacts with phenylphosphonic dichloride to afford a mixture of diastereoisomeric bicyclic oxazaphospholes in 80-90% yield, easily separated by flash chromatography. Koizumi, T., Yanada, R.; Takagi, H.; Hirai, H.; Yoshii, E. Tetrahedron Lett. 1981, 571-572.
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18. 4 After removing of the solvent, the pure alcohol is obtained by distillation on a Kugelrohr apparatus.
19. 31p -NMR spectra clearly indicates the formation of different borane complexes derived from 7 : the peak at 38 ppm corresponding to 6 disappeared and new signals at 80-100 ppm were detected.
20. See : Jacques, J.; Gros, C.; Boursier, S. Stereochemistry, vol. 4 "Absolute Configurations. One Asymmetric Carbon". Kagan, H. B. Ed; Georg Thieme Verlag Publishers : Stuttgart 1977.