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Pure Appl. Chem., 2007, Vol. 79, No. 2, pp. 213-221

Enantioenriched cyanohydrin O-phosphates: Synthesis and applications as chiral building blocks

Alejandro Baeza1, José M. Sansano1, José M. Saá2 and Carmen Nájera1

1 Departamento de Química Orgánica e Instituto de Síntesis Orgánica (ISO), Universidad de Alicante, Apdo. 99, E-03080 Alicante, Spain
2 Departamento de Química, Universitat de les Illes Balears, 07122 Palma de Mallorca, Spain

Abstract: Aluminum complexes of the chiral (R)- or (S)-3,3'-bis(diethylaminomethyl)-1,1'-bi-2,2'-naphthol (BINOLAM) ligand behave as efficient catalysts for the enantioselective cyanation-O-functionalization of aldehydes, thereby leading to enantiomerically enriched O-silyl, O-methoxycarbonyl, or O-phosphate derivatives of cyanohydrins. The enantioenriched cyanohydrin-O-phosphates are useful for the synthesis of several enantioenriched compounds such as α-hydroxy esters, β-amino alcohols, and γ-substituted α,β-unsaturated nitriles. Natural products such as (-)-aegeline and (-)-tembamide have been prepared in this manner.