α′-hydroxy Enones as Achiral Templates for Lewis Acid-Catalyzed Enantioselective Diels - Alder Reactions

Journal of the American Chemical Society

Volumn 125, Issue 46, 2003, Pages 13942-13943

  Palomo, Claudio ^a   Oiarbide, Mikel ^a   García, Jesús M ^b   González, Alberto ^b   Arceo, Elena ^b  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b PUBLIC UNIVERSITY OF NAVARRE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; CERIUM; CERIUM AMMONIUM NITRATE; KETONE DERIVATIVE; LEWIS ACID; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC CATALYSIS; CARBON NUCLEAR MAGNETIC RESONANCE; CHIRALITY; COMPLEX FORMATION; CYCLOADDITION; DIELS ALDER REACTION; METAL BINDING; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0242582901     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0368002     Document Type: Article

References (36)

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34. In the case of isoprene, the remaining catalysts 1b, 1c, and 2-3 were inferior (catalyst; ee: 1b; 8%. 1c; 18%. 2a; 24%. 2b; 32%. 3a; 26%).
35. Enones 10-13 were readily prepared by aldol condensation of the commercially available 3-hydroxy-3-methyl-2-butanone with the respective aldehyde. See Supporting Information for details.
36. Other less reactive dienes such as isoprene and 2,3-dimethylbutadiene did not react with β-substituted enones under the conditions tested.