American Chemical Society
ol0265620_si_002.pdf (181.21 kB)

A Novel C2-Symmetric 2,6-Diallylpiperidine Carboxylic Acid Methyl Ester as a Promising Chiral Building Block for Piperidine-Related Alkaloids

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journal contribution
posted on 2002-09-05, 00:00 authored by Hiroki Takahata, Hidekazu Ouchi, Motohiro Ichinose, Hideo Nemoto
C2-Symmetric 2,6-diallylpiperidine 1-carboxylic acid methyl ester (5) was examined via the double asymmetric allylboration of glutaraldehyde followed by aminocyclization and carbamation as a promising chiral building block for piperidine-related alkaloids, which were synthesized by the desymmetrization of 5 using intramolecular iodocarbamation as a key step.