Improvement in the Regioselectivity in the Ruthenium-catalyzed Metathesis Reaction of 2-Azabicyclo[2.2.1]hept-5-en-3-one (ABH) with Allyltrimethylsilane

Abstract

2-Azabicyclo[2.2.1]hept-5-en-3-one (ABH) (1) with N-trialkylsilyl group was subjected to a ring-opening cross-metathesis reaction with allyltrimethylsilane in the presence of a ruthenium catalyst, allowing the predominateformation of rel-(3R,5S)-3-(4,4,-dimethyl-4-silapentyl)-5-ethylpyrrolidin-2-one (5) over rel-(3R,5S)-5-(4,4,-dimethyl-4-silapentyl)-3-ethylpyrrolidin-2-one (6).