Synthesis of. alpha.-hydroxy ketones by samarium (II) iodide-mediated coupling of organic halides, an isocyanide, and carbonyl compounds

M Murakami, T Kawano, H Ito, Y Ito

Index: Murakami, Masahiro; Kawano, Teiji; Ito, Hajime; Ito, Yoshihiko Journal of Organic Chemistry, 1993 , vol. 58, # 6 p. 1458 - 1465

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Citation Number: 43

Abstract

A new strategy for the synthesis of a-hydroxy ketones by samarium (I1) iodide-mediated threecomponent coupling of organic halides, an isocyanide, and carbonyl compounds is disclosed. An (a-iminoalkyl) samarium (III) species is generated in situ by treatment of an organic halide with 2 equiv of samarium (I1) iodide in the presence of 2, 6-xylyl isocyanide. Subsequent treatment of the mixture with a carbonyl compound affords a-hydroxy imines, ...