On the Reactivity of Ferrocenoylsilanes

Abstract

Reactions of ferrocenoylsilanes 1 with lithium aluminium hydride and organometallic reagents show unusual behaviour in that the ferrocenyl aldehydes 4 and ketones 5−9 are obtained instead of the expected secondary and tertiary silylated alcohols. This paper also reports on the synthesis and reactivity of the first planar chiral enantiomerically pure ferrocenoylsilane 1d that offers the possibility of synthesizing planar chiral enantiomerically pure 1,2-disubstituted aldehyde 4b and ketones 5b, 6b, 7b, 8 and 9. A mechanistic hypothesis is proposed for explaining the obtained results.