Synthesis and further reactivity of functionalized lactam-derived enol triflates

T Luker, H Hiemstra, WN Speckamp

Index: Luker, Tim; Hiemstra, Henk; Nico Speckamp Journal of Organic Chemistry, 1997 , vol. 62, # 23 p. 8131 - 8140

Full Text: HTML

Citation Number: 60

Abstract

Pyrrolidinone-and piperidinone-derived enol triflates 2 were prepared in high yield (60-97%) from the corresponding lactams 1 using KHMDS and N-(5-chloro-2-pyridyl) triflimide. A structure-stability study on the less stable pyrrolidinone-derived triflates revealed that an N- tosyl group is essential, and an α-ethoxy substituent enhances thermal stability. Substituents at the 3-and 4-position are tolerated. Substitution of the triflate moiety by a wide variety of ...