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


  • This work was supported by the DGES of the Spanish Ministerio de Ciencia y Tecnología (PB97–0123 and BQU2001–0724-C02-) and by Generalitat Valenciana (CTIOIB/2002/320). A.B. also thanks Generalitat Valenciana for a predoctoral fellowship.


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(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).