Asymmetric Synthesis Using Chiral Acetals : Highly Diastereoselective Addition of Organocerium Reagents to Chiral α-Aldoxime-Ether Acetal

Hiromichi FUJIOKA; Masahiro FUJI; Yoshihiko OKAICHI; Takayuki YOSHIDA; Hirokazu ANNOURA; Yasuyuki KITA; Yasumitsu TAMURA

doi:10.1248/cpb.37.602

Hiromichi FUJIOKA, Masahiro FUJI, Yoshihiko OKAICHI, Takayuki YOSHIDA, Hirokazu ANNOURA, Yasuyuki KITA, Yasumitsu TAMURA

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Keywords: asymmetric synthesis, diastereoselective nucleophilic addition, chiral aldoxime-ether acetal, (-)-(2S, 3S)-1, 4-dimethoxy-2, 3-butanediol, organocerium reagent, N-oxygenated chiral amine, (-)-N-acetylamphetamine

JOURNAL FREE ACCESS

1989 Volume 37 Issue 3 Pages 602-605

DOI https://doi.org/10.1248/cpb.37.602

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Abstract

Nucleophilic addition of organometallic reagents [organocerium reagents (RMgX-CeCl₃, RLi-CeCl₃), Grignard reagent, and organolithium reagents] to the chiral α-aldoxime-ether acetal (1) was studied.Among the reagents, organocerium reagents showed higher reactivity and stereoselectivity, giving the N-oxygenated chiral amine derivatives (6Aa-c) in a highly diastereoselective manner, whereas Grignard and organolithium reagents afforded no 6.As an application of the reaction, the synthesis of (-)-N-acetylamphetamine (11) was achieved.

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