Asymmetric, catalytic phenyl transfer to imines: Highly enantioselective synthesis of diarylmethylamines

Angewandte Chemie - International Edition

Volumn 41, Issue 19, 2002, Pages 3692-3694

  Hermanns, Nina ^b   Dahmen, Stefan ^b   Bolm, Carsten ^b   Bräse, Stefan ^a  

^a UNIVERSITY OF BONN   (Germany)

^b RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

Cyclophanes; Enantioselectivity; Homogeneous catalysis; Imines; Zinc

Indexed keywords

CATALYSIS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVE SYNTHESIS;

ORGANIC COMPOUNDS;

CETIRIZINE; CYRHETRENE; FERROCENE DERIVATIVE; IMINE; METHYLAMINE; PHENYL GROUP; PHENYLZINC; TOLUENE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ARTICLE; CATALYSIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS;

EID: 0037020423     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021004)41:19<3692::AID-ANIE3692>3.0.CO;2-N     Document Type: Article

References (40)

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35. The [2.2]paracyclophane-based N,O-ligands have previously been employed in the dialkylzinc and the alkenylzinc addition to aldehydes: a) S. Dahmen, S. Bräse, Chem. Commun. 2002, 26; b) S. Dahmen, S. Bräse, Org. Lett. 2001, 3, 4119; c) for the synthesis of compounds 4 and 6, see V. Rozenberg, T. Danilova, E. Sergeeva, E. Vorontsov, Z. Starikova, K. Lysenko, Y. Belokon, Eur. J. Org. Chem. 2000, 3295.
36. The [2.2]paracyclophane-based N,O-ligands have previously been employed in the dialkylzinc and the alkenylzinc addition to aldehydes: a) S. Dahmen, S. Bräse, Chem. Commun. 2002, 26; b) S. Dahmen, S. Bräse, Org. Lett. 2001, 3, 4119; c) for the synthesis of compounds 4 and 6, see V. Rozenberg, T. Danilova, E. Sergeeva, E. Vorontsov, Z. Starikova, K. Lysenko, Y. Belokon, Eur. J. Org. Chem. 2000, 3295.
37. The [2.2]paracyclophane-based N,O-ligands have previously been employed in the dialkylzinc and the alkenylzinc addition to aldehydes: a) S. Dahmen, S. Bräse, Chem. Commun. 2002, 26; b) S. Dahmen, S. Bräse, Org. Lett. 2001, 3, 4119; c) for the synthesis of compounds 4 and 6, see V. Rozenberg, T. Danilova, E. Sergeeva, E. Vorontsov, Z. Starikova, K. Lysenko, Y. Belokon, Eur. J. Org. Chem. 2000, 3295.
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39. The absolute configurations of all other products should be R as well if an analogous stereochemical reaction pathway is assumed.
40. Attempts to determine the enantiomeric excess of amine 10b itself by means of HPLC on a chiral stationary phase were unsuccessful.