A multifunctional proline-based organic catalyst for enantioselective aldol reactions

Tetrahedron Asymmetry

Volumn 17, Issue 19, 2006, Pages 2754-2760

  Guizzetti, Stefania ^a   Benaglia, Maurizio ^a   Pignataro, Luca ^a   Puglisi, Alessandra ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,1' BINAPHTHYL 2,2' DIAMINE; ACETONE; ALDEHYDE DERIVATIVE; AMIDE; CYCLOHEXANONE; DIAMINE DERIVATIVE; KETONE DERIVATIVE; METHOXYACETONE; PROLINAMIDE DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYST; ENANTIOSELECTIVITY; POLYMERIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 33751159838     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.10.018     Document Type: Article

References (40)

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31. This result is also in good agreement with the one reported in Ref. 10c where an analogous N-benzoyl derivative promoted the aldol condensation in acetone at 4 °C in 83% ee.
32. Catalysts 3 and 5 promoted the reaction in acetone with slightly lower enantioselectivity.
33. The role of the stereogenic axis of binaphthyl diamine is currently under active investigation in our group. Preliminary studies showed that 1,1′-biphenyl-2,2′-diamine-based prolinamides catalysed the aldol condensation with slightly lower enantioselectivities than binaphthyl diamine-based prolinamides. Please note that also Gryko reported contradictory results in acetone and dioxane as reaction solvents that prevent any easy determination of the matching configurations of the stereogenic elements of the molecule.
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35. 2 symmetric ones in DMF (dr >99/1, 95% ee vs dr 10/1, 93% ee, see Ref. 10a).
36. It is worth mentioning that under the same experimental conditions, the use of hydroxyacetone brought us to the formation of racemic products. However the use of catalyst 2 in DMSO allowed to obtain the anti-isomer in 82% ee (see Ref. 10b). Please note that catalyst 2 in DMF at 0 °C promoted the reaction with methoxyacetone in 92% ee (see Ref. 10b).
37. The reaction with benzaldehyde and cyclohexanecarboxaldehyde did not afford the product in reasonable yield.
38. The role of addictives in the Mannich reaction and different experimental conditions in order to improve the enantioselectivity of the process are currently under study.
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