Organic letters

Hexafluoroisopropanol as a Unique Solvent for Stereoselective Iododesilylation of Vinylsilanes

EA Ilardi, CE Stivala, A Zakarian

Index: Ilardi, Elizabeth A.; Stivala, Craig E.; Zakarian, Armen Organic Letters, 2008 , vol. 10, # 9 p. 1727 - 1730

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Citation Number: 55

Abstract

Previously, the Kishi group reported a method for a mild preparation of vinyliodides from vinylsilanes using N-iodosuccinimide (NIS) and a 9:1 mixture of acetonitrile and chloroacetonitrile as the solvent.(14) A high stereoselectivity was observed with many substrates, but simple vinylsilanes gave a mixture of products with modest stereocontrol. For example, (E)-1-trimethylsilyl-1-octene and (Z)-1-trimethylsilyl-1-octene provided mixtures of the corresponding (E)- and (Z)- ...