Enantioselective addition of diethylzinc to benzaldehyde catalyzed by ferrocenic amino-alcohols combining centered and planar chiralities

Tetrahedron Asymmetry

Volumn 10, Issue 17, 1999, Pages 3253-3257

  Malézieux, Bernard ^a   Andrés, Román ^a   Gruselle, Michel ^a   Rager, Marie Noëlle ^b   Thorimbert, Serge ^a  

^a SORBONNE UNIVERSITÉ   (France)

^b 11 R P et M Curie 75231 Cedex 05   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BENZALDEHYDE; DIETHYLZINC; FERROCENE DERIVATIVE; PROPANOL;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0038398618     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00307-9     Document Type: Article

References (22)

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17. 3 to extract the catalyst) had the consequence of altering the catalyst. We obtained in this way the very clean transformation of the (-)-(pS,3S,4R)-1 into another enantiomerically pure amino-alcohol presumably (+)-(pS,3S,4S) as a consequence of a benzylic isomerization. This compound was previously observed and described as a minor product in the synthesis of 1 and 2 (see Ref. 12). This compound is also a catalyst but less efficient than 1 or 2 (a 3% molar ratio gives the (S)-phenyl propanol with 41% yield and in 52% ee).
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22. 2 lead to the displacement to a unique conformer. This fact is indicated by the evolution of a single peak related to the cyclopentadienyl moiety.