Tetrahedron Letters

A new synthetic route to 3-polyfluoroalkyl-containing pyrroles

EN Shaitanova, II Gerus, VP Kukhar

Index: Shaitanova, Elena N.; Gerus, Igor I.; Kukhar, Valery P. Tetrahedron Letters, 2008 , vol. 49, # 7 p. 1184 - 1187

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Citation Number: 19

Abstract

A novel approach to 3-polyfluoroalkyl pyrroles is reported based on step by step reactions: 1, 2-addition of Me3SiCN to β-alkoxyvinyl polyfluoroalkyl ketones, reduction with LiAlH4 and subsequent hydrolysis with intramolecular cyclization. The hydrolytic instability of various polyfluoroalkyl groups at position 3 of the pyrrole ring was evident and a pathway for the hydrolysis was proposed.