On The Metalation-Silylation of O-Trimethylsilyl Aldehyde Cyanohydrins

Article abstract of DOI:10.1021/jo00030a030

The metalation-trimethylsilylation of O-trimethylsilyl (saturated) aldehyde cyanohydrins was achieved by in situ treatment with LDA and trimethylchlorosilane at -78 deg C.C-Silyl products (O-trimethylsilyl acylsilane cyanohydrins) generally predominated, but N-silyl derivatives (ketenimines) were found in some instances.LDA could be added across the C=N bond of the latter.The metalation-trimethylsilylation o O-trimethylsilyl benzaldehyde cyanohydrin could only be effected if 2 equiv of trimethylchlorosilane were employed per equivalent of cyanohydrin anion.