The Journal of Organic Chemistry

The metalation-silylation of O-trimethylsilyl aldehyde cyanohydrins

RF Cunico, CP Kuan

Index: Cunico, Robert F.; Kuan, Chia P. Journal of Organic Chemistry, 1992 , vol. 57, # 4 p. 1202 - 1205

Full Text: HTML

Citation Number: 17

Abstract

The metalation-trimethylsilylation of 0-trimethylsilyl (saturated) aldehyde cyanohydrins was achieved by in situ treatment with LDA and trimethylchlorosilane at-78 OC. C-Silyl products (0-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 of 0-trimethylsilyl benzaldehyde cyanohydrin ...