Tetrahedron p. 10699 - 10714 (1995)
Update date:2022-08-03
Topics:
Enders, Dieter
Plant, Andrew
Backhaus, Dirk
Reinhold, Ulrich
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%).
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