Palladium catalysed allylic acetoxylation of dialkyl allyl phosphonates

Tetrahedron

Volumn 52, Issue 6, 1996, Pages 2087-2096

  Principato, Bruno ^a   Maffei, Michel ^a   Siv, Chhan ^a   Buono, Gérard ^a   Peiffer, Gilbert ^a  

^a AIX MARSEILLE UNIVERSITY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030053970     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01046-7     Document Type: Article

References (37)

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23. Only the relative position of the phosphonate group determines the stereoselectivity of the reaction, as shown in the following scheme. (formula presented) Syn (π-allyl) palladium complexes I and III give rise to the E isomer, while Z isomer results from anti complexes II and IV. Thus, syn/anti isomerisation can also occur on the γ position, but this phenomenon does not influence the E/Z ratios.
24. In a control experiment, pure (E) and (Z) diethyl 3-acetoxy 1-propenyl phosphonates were separately subjected to the acetoxylation conditions (see experimental, 65°C, overnight). No isomerisation occured in both cases, indicating that there is no thermodynamic equilibrium between the two isomeric acetates under the reactions conditions. Therefore, the stereochemical outcome of the reaction cannot be modified by such a process.
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37. 13