Enantioselective Synthesis of Cyanohydrin O-Phosphates Mediated by the Bifunctional Catalyst Binolam-AlCl

(R)‐ and (S)‐binolam–AlCl complexes act as bifunctional catalysts to mediate the enantioselective cyanophosphorylation of aldehydes at room temperature. The resulting chiral cyanohydrin O‐phosphates can be reduced to β‐aminoalcohols or, when suitably substituted, can be transformed into γ‐cyanoallyl...

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Veröffentlicht in:Angewandte Chemie International Edition 2003-07, Vol.42 (27), p.3143-3146
Hauptverfasser: Baeza, Alejandro, Casas, Jesús, Nájera, Carmen, Sansano, José M., Saá, José M.
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Sprache:eng
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Zusammenfassung:(R)‐ and (S)‐binolam–AlCl complexes act as bifunctional catalysts to mediate the enantioselective cyanophosphorylation of aldehydes at room temperature. The resulting chiral cyanohydrin O‐phosphates can be reduced to β‐aminoalcohols or, when suitably substituted, can be transformed into γ‐cyanoallylic alcohols through palladium‐catalyzed allylic substitution, without loss of enantiomeric excess (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351552