Asymmetric [2,3]-sigmatropic Wittig rearrangement of chiral alpha-allyloxy-hydrazones

被引：27
作者：
Enders, D
Backhaus, D
Runsink, J
机构：
[1] Institut für Organische Chemie, Rheinisch-Westfälische TH, D-52074 Aachen
来源：
TETRAHEDRON | 1996年 / 52卷 / 05期
关键词：
D O I：
10.1016/0040-4020(95)00982-5
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The asymmetric [2,3]-Wittig rearrangement of chiral alpha-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 alpha-hydroxyhydrazones 4 and 8. Depending on the substitution patterns of the starting material, optically active aliphatic and aromatic alpha-hydroxyketones 5 or protected cyanohydrins 10 and alpha-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.
引用
收藏
页码：1503 / 1528
页数：26
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