Highly enantioselective organocatalytic conjugate addition of malonates to acyclic α,β-unsaturated enones

Angewandte Chemie - International Edition

Volumn 42, Issue 6, 2003, Pages 661-665

  Halland, Nis ^a   Aburel, Pompiliu S ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Asymmetric catalysis; Enones; Ketoesters; Malonates; Tetrahydroquinolines

Indexed keywords

ADDITION REACTIONS; CATALYST ACTIVITY; ESTERS; SYNTHESIS (CHEMICAL);

ENANTIOSELECTIVITY;

UNSATURATED COMPOUNDS;

ESTER; IMIDAZOLIDINE DERIVATIVE; MALONIC ACID; PHENYLALANINE; QUINOLINE DERIVATIVE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; ENANTIOSELECTIVITY; MICHAEL ADDITION; REACTION OPTIMIZATION;

EID: 0037429423     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390182     Document Type: Article

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56. 2O to the reaction mixture did not affect yield of enantioselectivity.
57. CCDC-194337 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ ccdc.cam.ac.uk).
58. The calculations have been performed for the protonated carboxylic acid form of 5.
59. For a recent racemic synthesis of tetrahydroquinolines and their biological activity, see R. A. Bruce, D. M. Herron, L. B. Johnson, S. V. Kotturi, J. Org. Chem. 2001, 66, 2822, and references therein.