Stereoselective cyanohydrin-forming reactions of chiral α-amino aldehydes

Reetz, M. T.; Drewes, M. W.; Harms, K.; Reif, W.

doi:10.1016/0040-4039(88)85144-X

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Stereoselective cyanohydrin-forming reactions of chiral α-amino aldehydes

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引用

Reetz, M. T., Drewes, M. W., Harms, K., & Reif, W. (1988). Stereoselective cyanohydrin-forming reactions of chiral α-amino aldehydes. Tetrahedron Letters, 29(27), 3295-3298. doi:10.1016/0040-4039(88)85144-X.

引用: https://hdl.handle.net/21.11116/0000-000E-7CFD-B

要旨

The Lewis acid mediated cyanohydrin-forming addition of Me₃SiCN to optically active α-dibenzylamino aldehydes 2 occurs stereoselectively. Chelation controlled adducts 3 result if MgBr₂ or TiCl₄ is used, whereas the diastereomers 4
are obtained upon employing BF₃, ZnBr₂ or SnCl₄.

Aldehydes 2 react with Me₃SiCN to form either 3 or 4, depending upon the Lewis acid used.