A Convenient Synthesis of 2,2-Diallylated Nitrogen Heterocycles by Allylboration of Lactams

Abstract

Lactams containing an N‐H bond are smoothly transformed into 2,2‐diallylated nitrogen heterocycles on heating with allylic boranes in THF followed by deboronation

Adducts of Triallylborane with Ammonia and Aliphatic Amines as Stoichiometric Allylating Agents for Aminoallylation Reaction of Carbonyl Compounds

“…Homoallylamines are versatile and useful synthetic intermediates in the pharmaceutical chemistry and in the synthesis of natural products and heterocyclic compounds . The most powerful allylborating agents for synthesis of homoallylamines are tri- and monoallylic organoboranes, which are capable of allylborating an array of compounds with multiple C–N bonds. − Allylic organoboranes are highly reactive and react with imines at temperatures as low as −100 °C, providing excellent enantioselectivity with chiral organoboranes . One of the most important advantages of triallylic boranes along with their activity is their atomic efficiency.…”