Tetrahedron Letters

Reaction of cyanotrimethylsilane with oxiranes under Yb (CN) 3 catalysis

S Matsubara, H Onishi, K Utimoto

Index: Matsubara, Seijiro; Onishi, Hitoshi; Utimoto, Kiitiro Tetrahedron Letters, 1990 , vol. 31, # 43 p. 6209 - 6212

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Citation Number: 54

Abstract

Reaction of R 3 Yb, prepared from YbCl 3 and RLi, with Me 3 SiCN gives Yb(CN) 3 , which is a highly efficient catalyst for regio and stereoselective cleavage of an oxirane with Me 3 SiCN under mild conditions to give a β-trimethylsiloxy nitrile in excellent yield. ... Ln(CN) 3 (Ln: Sc, Y, Ce, Eu) is also effective for the reaction. ... Silicon Reagents for Organic SynthesisSpringer-Verlag, Berlin (1983) Chapter 2. ... J. Org. Chem., 52 (1987), p. 1013 ...

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