Diastereoselective Palladium-Catalyzed Formate Reduction of Allylic Carbonates as a New Entry into Propionate Units

Organic Letters

Volumn 5, Issue 19, 2003, Pages 3391-3394

  Lautens, Mark ^a   Paquin, Jean François ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; ALKENE; ALPHA METHYL BETA,GAMMA UNSATURATED ALDEHYDE; CARBONIC ACID; CHEMICAL COMPOUND; PALLADIUM; POLYPRIONATE; PROPIONIC ACID; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL REACTION; ISOMER; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0345171569     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0350238     Document Type: Article

References (48)

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27. 2Cs) were not as effective, probably due to their low solubility.
28. 1H NMR spectroscopy. For the purpose of this study, > 15:1 dr indicates that the other diastereomer was present in less than 6% (typically 4-6%), whereas > 20:1 dr specifies that the other diastereomer was not detectable.
29. On a 0.2 mmol scale, the reaction with 2.5 mol % Pd at room temperature led to almost complete conversion after 3 days, compared to < 1 h at 40°C. On a 0.5 mmol scale, the reaction with 2.5 mol % Pd is done in < 2 h.
30. Stereochemistry of the products was determined by comparison with authentic samples or similar or previously reported compounds; see Supporting Information for details.
31. Under the optimized conditions, other leaving groups such as acetate or formate (see ref 1c) gave incomplete conversion and no reaction, respectively.
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34. 13C NMR spectroscopy
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