Stereoselective synthesis and use in catalytic asymmetric addition of diethylzinc to benzaldehyde of new chiral amino alcohol complexes: Influence of the chromium complexation on the enantioselectivity

Tetrahedron Asymmetry

Volumn 7, Issue 3, 1996, Pages 653-656

  Malfait, Stéphane ^a   Pélinski, Lydie ^a   Brocard, Jacques ^a  

^a UNIV LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANOL; INDAN DERIVATIVE; INDANOL; PHENYLPROPANOL; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029960269     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00056-0     Document Type: Article

References (28)

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15. The nomenclature followed the attribution of the configuration described by previous literature: Schlögl, K. Topics in stereochemistry, 1967, 1, 39.
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19. Determined by optical rotation. (see Jaouen, G and al., ref. 12)
20. 12.(a) Jaouen, G.; Meyer, A. J. Am. Chem. Soc. 1975, 97, 4667.
21. (b) Top, S.; Meyer, A.; Jaouen, G. Tetrahedron Lett. 1979, 3537.
22. 2O + TMS) δ 5.7 (d, J = 6.1 Hz, 1H), 5.4 (t, J = 6.1 Hz, 1H), 5.2 (d, J = 6.1 Hz, 1H), 51 (t, J = 6.1 Hz, 1H), 2.75 (m, 2H), 2.3 (s, 6H), 2.3 - 2.4 (m, 2H), 2.2 (m, 2H), 1.2 (s, 3H), 0.6 (s, 3H).
23. 3 + TMS) δ 8.5 (d, J = 5.0 Hz, 1H); 7.7 (t, J = 5.0 Hz, 2H); 7.2 (t, J = 5.0 Hz, 2H); 5.5 (d, J = 6.1 Hz, 1H); 5.4 (t, J = 6.1 Hz, 1H); 5.3 (d, J = 6.1 Hz, 1H); 5.1 (t, J = 6.1 Hz, 1H); 3.0 (m, 2H); 2.5 (m, 2H).
24. Bolm, C.; Zehnder, M.; Bur, D. Angew. Chem. Int. Ed. Engl., 1990, 29, 205-207.
25. Wakefield, B.J. In Organolithium Methodes; Academic Press, 1988, p 27 - 51.
26. 2O + TMS) δ 8.5 (m, 1H); 7.6 (m, 1H); 7.2 (m, 1H); 7.0 (m, 1H); 5.3 (t, J = 6.3 Hz, 1H); 5.2 (d, J = 6.3 Hz, 1H); 5.1 (d, J = 6.3 Hz, 0H); 5.0 (t, J = 6.3 Hz, 1H); 3.1 (dd, J = 21 Hz and J = 14 Hz, 2H); 2.7 (m, 2H); 2.1 (m, 2H).
27. 3 + TMS) δ 7.1 (m, 2H); 6.7 (m, 2H); 5.6 (d, J = 6.2 Hz, 1H); 5.5 (t, J = 6.2 Hz, 1H); 5.3 (d, J = 6.2 Hz, 1H); 5.1 (t, J = 6.2 Hz, 1H); 2.8 (s, 6H); 2.2 - 2.6 (m, 4H).
28. General Procedure: Under nitrogen, diethylzinc was added to a solution of benzaldehyde and the chiral complex (5 mol %) in dry toluene. The reaction mixture was stirred at room temperature and the progress of the reaction was monitored by GC. After work up, the residue was isoled by colomn chromatography to give 1-phenylpropanol.