Tetrahedron letters

Synthesis of vinyl fluorides by ring-closing metathesis

M Marhold, A Buer, H Hiemstra, JH van Maarseveen…

Index: Marhold, Michael; Buer, Anna; Hiemstra, Henk; Van Maarseveen, Jan H.; Haufe, Guenter Tetrahedron Letters, 2004 , vol. 45, # 1 p. 57 - 60

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Citation Number: 54

Abstract

The first ring-closing olefin metatheses of alkenyl α-fluoroacrylamides or acrylates incorporating a fluorinated double bond are reported. Several N-benzyl-N-alkenyl-α- fluoroacrylamides were cyclized in the presence of 2mol% of Grubbs II catalyst at room temperature to form an unsaturated γ-lactam, and at 80° C to form the corresponding δ- lactams bearing a fluoro vinyl moiety. At elevated temperature, cyclization of an N- ...