The first organocatalytic enantioselective inverse-electron-demand hetero-Diels-Alder reaction

Angewandte Chemie - International Edition

Volumn 42, Issue 13, 2003, Pages 1498-1501

  Juhl, Karsten ^a   Jørgensen, Karl Anker ^a  

^a AARHUS UNIVERSITY   (Denmark)

Author keywords

Aldehydes; Amines; Asymmetric catalysis; Cycloaddition; Enones

Indexed keywords

ALDEHYDES; CATALYSTS; CHEMICAL REACTIONS; KETONES;

ORGANOCATALYTIC REACTIONS;

ORGANOMETALLICS;

AMINE; ENAMINE; PYRROLIDINE DERIVATIVE;

ARTICLE; CATALYSIS; DIELS ALDER REACTION; ELECTRON; ENANTIOSELECTIVITY; HYDROLYSIS; STEREOCHEMISTRY;

EID: 0344835672     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200250652     Document Type: Article

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43. The Lewis acid catalyzed enantioselective hetero-Diels-Alder reaction of electron-rich alkenes with electron-poor enones has been developed: a) K. A. Jørgensen, Angew. Chem. 2000, 112, 3702; Angew. Chem. Int. Ed. 2000, 39, 3559; b) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325; c) K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain, J. Thorhauge, Acc. Chem. Res. 1999, 32, 605; see also: d) K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2002, 114, 3185; Angew. Chem. Int. Ed. 2002, 41, 3059.
44. The Lewis acid catalyzed enantioselective hetero-Diels-Alder reaction of electron-rich alkenes with electron-poor enones has been developed: a) K. A. Jørgensen, Angew. Chem. 2000, 112, 3702; Angew. Chem. Int. Ed. 2000, 39, 3559; b) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325; c) K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain, J. Thorhauge, Acc. Chem. Res. 1999, 32, 605; see also: d) K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2002, 114, 3185; Angew. Chem. Int. Ed. 2002, 41, 3059.
45. The Lewis acid catalyzed enantioselective hetero-Diels-Alder reaction of electron-rich alkenes with electron-poor enones has been developed: a) K. A. Jørgensen, Angew. Chem. 2000, 112, 3702; Angew. Chem. Int. Ed. 2000, 39, 3559; b) J. S. Johnson, D. A. Evans, Acc. Chem. Res. 2000, 33, 325; c) K. A. Jørgensen, M. Johannsen, S. Yao, H. Audrain, J. Thorhauge, Acc. Chem. Res. 1999, 32, 605; see also: d) K. Gademann, D. E. Chavez, E. N. Jacobsen, Angew. Chem. 2002, 114, 3185; Angew. Chem. Int. Ed. 2002, 41, 3059.
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48. The stoichiometric HDA reaction of achiral enamines with β,γ-unsaturated-α-ketoesters has been reported earlier: F. Eiden, W. Winkler, Arch. Pharm. 1986, 319, 704. Schreiber et al. have used a stoichiometric asymmetric enamine-enal cycloaddition for the synthesis of a series of brefeldin isomers: S. L. Schreiber, H. V. Meyers, J. Am. Chem. Soc. 1988, 110, 5198.
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50. In all cases, only one diastereomer of 8 was detected, with the exception of 8ac (d.r. = 45:1).
51. CCDC-198535 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).