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Abstract
The asymmetric [2,3]-Wittig rearrangement of chiral α-allyloxy-hydrazones ( S)-3 and ( S)-7 proceeds with very good yields (72 – 100%) together with high syn-selectivities (87 – 97%) and asymmetric inductions (63 – 92%) to give the corresponding α-hydroxyhydrazones 4 and 8. Depending on the substitution patterns of the starting material, optically active aliphatic and aromatic α-hydroxyketones 5 or protected cyanohydrins 10 and α-hydroxyaldehydes 11 respectively, can be generated in high enantiomeric excesses (92 – 98%) and syn-selectivities (88 – > 99%) after chromatographic purification and removal of the auxiliary.
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