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Communication | Special issue | Vol 56, No. 1-2, 2002, pp.97-100
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)46
■ Asymmetric Synthesis of Tetrahydroquinoline Derivative, a Building Block of Martinellines, via Intramolecular Allylic Amination Using 9-PBN

Yasumasa Hamada,* Iyo Kunimune, and Osamu Hara

*Graduate School of Pharmaceutical Sciences, Chiba University, 1-33 Yayoi-cho, Inage-ku, Chiba 263-8522, Japan

Abstract

A tetrahydroquinoline derivative, a core structure of martinellines, was prepared through intramolecular allylic amination of the racemic precursor with a stereogenic center using 9-PBN and palladium. The reaction proceeded in a reagent-controlled manner based on the chiral phosphine to give two diastereomeric products with moderate enantioselectivities.