Ap. Johnson et al., REACTIONS OF 1-ACYLAMINO-1-(TRIMETHYLSILOXY)ALKANES - VERSATILE PRECURSORS TO ACYLIMINES, Journal of the Chemical Society. Perkin transactions. I, (9), 1996, pp. 895-905
1-Acylamino-1-(trimethylsiloxy)alkanes react with carbon and heteroato
m nucleophiles to give the corresponding 1-substituted-1-acylaminoalka
nes. The 1-acylamino-1-(trimethylsiloxy)alkanes can also give rise to
enamides, and by this route the mild antibiotic tuberin, and the isome
ric (Z)-tuberin have been prepared. A further example of their reactio
ns is illustrated with the acid-catalysed intramolecular cyclisation o
nto a carbon-carbon double bond, These transformations show that 1-acy
lamino-1-(trimethylsiloxy)alkanes are versatile precursors to syntheti
cally useful acylimines.