Tetrahedron letters

Reaction of indium ate complexes with allylic compounds. Controlling SN 2/SN 2′ selectivity by solvents

T Hirashita, Y Hayashi, K Mitsui, S Araki

Index: Hirashita, Tsunehisa; Hayashi, Yousuke; Mitsui, Kazuma; Araki, Shuki Tetrahedron Letters, 2004 , vol. 45, # 16 p. 3225 - 3228

Full Text: HTML

Citation Number: 13

Abstract

Vinyl and methylindium ate complexes (indates) were prepared and both the tendency of immigration and regioselectivity toward cinnamyl bromide were investigated. The vinyl group was more preferably transferred than the Me group, giving a regioisomeric mixture of SN2 and SN2′ products. The ratio of SN2/SN2′ selectivity can be controlled by solvents; in the presence of polar solvents, such as N-butylpyrrolidone (NBP) and THF, the SN2′ ...