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

Item

ITEM ACTIONSEXPORT

Add to Basket

Local TagsRelease HistoryDetailsSummary

Released

Journal Article

Stereoselective cyanohydrin-forming reactions of chiral α-amino aldehydes

MPS-Authors

There are no MPG-Authors in the publication available

External Resource

No external resources are shared

Fulltext (restricted access)

There are currently no full texts shared for your IP range.

Fulltext (public)

There are no public fulltexts stored in PuRe

Supplementary Material (public)

There is no public supplementary material available

Citation

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.

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

Abstract

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.