Seebach's oxazolidinone is a good catalyst for aldol reactions

Tetrahedron Letters

Volumn 49, Issue 37, 2008, Pages 5414-5418

  Isart, Carles ^a   Burés, Jordi ^a   Vilarrasa, Jaume ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Aldol reactions; Bicyclic oxazolidinones; Organocatalysis; Proline

Indexed keywords

5 (PYRROLIDIN 2 YL)TETRAZOLE; CARBONYL DERIVATIVE; ENAMINE; KETONE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PROLINE; TETRAZOLE DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE;

EID: 48149111324     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.07.028     Document Type: Article

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37. tBuCHO.
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49. Compound 2d is so soluble that it can be used even in a larger excess, if it was needed.
50. 2.
51. 1H NMR (the probable equilibrium is too shifted to the left). This explains why 4d does not catalyse aldol reactions.
52. We have depicted 12d (in Scheme 3) as a representative of the four bicyclic stereoisomers (with different conformers) that can be formed as adducts.
53. Any aldehyde remaining in the reaction flask will do the same (see Supplementary data).
54. In the reactions of Table 1, the use of 2d means that species 1b/1c/1d, 2c/2d, 3c/3d and b/c/d-like derivatives of the reaction products (see, e.g., 12d in Scheme 3) can be all present in the equilibrium mixture. In spite of that, ca. 90% of 7 is formed (after 30-60 min!).