Tetrahedron: Asymmetry

A new asymmetric entry to 2-substituted piperidines. A concise synthesis of (+)-coniine,(−)-pelletierine,(+)-δ-coniceine, and (+)-epidihydropinidine

H Takahata, M Kubota, S Takahashi, T Momose

Index: Takahata, Hiroki; Kubota, Minoru; Takahashi, Seiki; Momose, Takefumi Tetrahedron Asymmetry, 1996 , vol. 7, # 10 p. 3047 - 3054

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Citation Number: 63

Abstract

A new asymmetric route to 2-substituted piperidines involving the Sharpless asymmetric dihydroxylation (AD) of 5-hexenylazide 1 and an intramolecular aminocyclization as crucial steps and its application to the asymmetric synthesis of four piperidine alkaloids,(+)-coniine 2,(−)-pelletierine 3,(+)-δ-coniceine 4, and (+)-epidihydropinidine 5 is presented.