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Communication | Regular issue | Vol 63, No. 1, 2004, pp.5-8
Published online, 14th November, 2003
DOI: 10.3987/COM-03-9924
Improvement in the Regioselectivity in the Ruthenium-catalyzed Metathesis Reaction of 2-Azabicyclo[2.2.1]hept-5-en-3-one (ABH) with Allyltrimethylsilane

Minoru Ishikura,* Miyako Hasunuma, and Makoto Saijo

*Faculty of Pharmaceutical Sciences, Health Sciences University of Hokkaido, Ishikari-Tobetsu, Hokkaido 061-0293, Japan

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 allyl-trimethylsilane in the presence of a ruthenium catalyst, allowing the predominate formation 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).