Organoselenium-induced cyclization of olefinic imidates and amides. Selective synthesis of lactams or iminolactones

A Toshimitsu, K Terao, S Uemura

Index: Toshimitsu, Akio; Terao, Keiji; Uemura, Sakae Journal of Organic Chemistry, 1987 , vol. 52, # 10 p. 2018 - 2026

Full Text: HTML

Citation Number: 60

Abstract

Ladams were formed selectively by the cyclization of olefinic imidates through the addition of a phenylseleno group to the double bond. Similar cyclization of olefinic amides, on the other hand, afforded either iminolactones or lactams depending on the structure of alkenyl moiety in the amides. The structure of lactams thus produced was confirmed by their lithium aluminum hydride reduction to nitrogen heterocycles. Iminolactones bearing a chloroalkyl ...