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.
Bonini B.F., Comes-Franchini M., Fochi M., Mazzanti G., Ricci A., Alberti A., et al. (2002). On the reactivity of ferrocenoylsilanes. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2002(3), 543-550 [10.1002/1099-0690(20022)2002:3<543::AID-EJOC543>3.0.CO;2-R].
On the reactivity of ferrocenoylsilanes
Bonini B. F.;Comes-Franchini M.;Fochi M.;Mazzanti G.;Ricci A.;Alberti A.;Marcaccio M.;Roffia S.
2002
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
