Asymmetric synthesis of α-substituted nitriles and cyanohydrins by oxidative cleavage of chiral aldehyde hydrazones with magnesium monoperoxyphthalate

Article abstract of DOI:10.1016/0040-4020(95)00647-Q

Optically active α- and α,β-substituted aldehyde hydrazones 2, 4, and 7, which are readily available by assymmetric alkylation, Michael addition or [2,3]-Wittig rearrangement of chiral hydrazones can be transformed into nitriles 3 and 5 or cyanohydrins 8 by MMPP mediated oxidation, respectively. This synthetic sequence offers a C-C connective entry into optically active functionalised nitriles with good overall yields (30-75%) together with high diastereo- and enantioselectivities (de = 76 - ≥ 96%, ee ≥ 72 - ≥ 97%).