Highly enantio- and diastereoselective organocatalytic asymmetric domino Michael-Aldol reaction of β-ketoesters and α,β-unsaturated ketones

Angewandte Chemie - International Edition

Volumn 43, Issue 10, 2004, Pages 1272-1277

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

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Aldol reaction; Domino reaction; Esters; Ketones; Michael addition

Indexed keywords

CATALYSIS; CATALYSTS; ORGANOMETALLICS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

BUILDING BLOCKS; DIASTEREOMERS; ENANTIOSELECTIVITY;

STEREOCHEMISTRY;

CYCLOHEXANONE DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; DIASTEREOISOMER; ENANTIOSELECTIVITY; MICHAEL ADDITION; STEREOCHEMISTRY;

EID: 2342614099     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200353364     Document Type: Article

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45. The 4,5-diphenyl-imidazolidine-2-carboxylic acid catalyst recently reported for the catalytic enantioselective formation of warfarin,[5] also promoted the domino Michael-aldol reaction in up to 90% ee in moderate yield.
46. CCDC-224447 (6a), CCDC-224448 (6c), and CCDC-224449 (6e) contain 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).
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50. The reaction rate is strongly concentration-dependent (see Supporting Information).