Synthesis and application of new (threo)- and (erythro)-amino alcohols based on the octahydro-cyclopenta[b]pyrrole system in the catalytic enantioselective addition of diethylzinc to benzaldehyde

Tetrahedron Asymmetry

Volumn 8, Issue 16, 1997, Pages 2761-2771

  Wilken, Jörg ^a   Gröger, Harald ^a   Kossenjans, Michael ^a   Martens, Jürgen ^a  

^a UNIVERSITY OF OLDENBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; BENZALDEHYDE; ZINC;

ARTICLE; CATALYST; CHEMICAL REACTION; DIASTEREOISOMER; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PURIFICATION; STEREOCHEMISTRY;

EID: 0342710334     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00327-3     Document Type: Article

References (24)

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11. (g) J. Wilken, J. Martens, Liebigs Ann./Recueil 1997, 563-571.
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13. 4Cl the resulting diastereomers were seperated by flash-chromatography. A more detailed description of this procedure is described in: J. Wilken, C. Thorey, H. Gröger, D. Haase, W. Saak, S. Pohl, J. Muzart, J. Martens, Liebigs Ann./Recueil 1997, in print.
14. (j) J. Eilers, J. Wilken, J. Martens, Tetrahedron: Asymmetry 1996, 8, 2343-2357.
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17. (m) S. Wallbaum, Ph.D. thesis, Universität Oldenburg, 1994.
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23. 2o,2p we used the optical purity o.p. instead of the enantiomeric excess e.e. to describe the catalytic efficiency of the amino alcohols in the diethylzinc addition to benzaldehyde. For the reason we observed a linear correlation between the o.p. and e.e. value for 1-phenylpropan-1-ol, in this paper we use for a better survey the correlated e.e. In general, the determination of optical purity is affected by a systematic error in the range of 2-4%; see: V. Schurig in: Houben-Weyl, Methods of Organic Chemistry, Workbench - Edition E2I, Vol. 1; Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Thieme, Stuttgart, 1996, p. 151-157.
24. K. Soai, A. Ookawa, T. Kaba, K. Ogawa, J. Am. Chem. Soc. 1987, 109, 7111-7115.