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Ytterbium tricyanide: Preparation and catalytic activity for the addition of cyanotrimethylsilane to carbonyl compounds

✍ Scribed by Kiitiro Utimoto; Tsutomu Takai; Yuri Kasuga; Seijiro Matsubara

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 521 KB
Volume: 9
Category: Article
ISSN: 0268-2605
DOI: 10.1002/aoc.590090507

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✦ Synopsis

Ytterbium tricyanide was obtained quantitatively by the reaction of ytterbium tri-isopropoxide with cyanotrimethylsilane. The addition of cyanotrimethylsilane to various carbonyl compounds was catalyzed effectively by ytterbium tricyanide to proceed under mild conditions giving the adducts in high selectivities. 2-Methylcyclohexanone yielded the adduct in a highly diastereoselective manner and the reagent system also effectively gave the adducts from easily enolizable ketones as well as from acid-sensitive ones. a,@-Unsaturated ketones and aldehydes afforded 1,2adducts exclusively.

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