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Zirconium-mediated SN2' substitution of allylic ethers: regio- and stereospecific formation of protected allylic amines.

ABSTRACT: A new zirconium-mediated, regio- and stereospecific SN2' substitution of allylic ethers with a nitrogen nucleophile has been developed. Cbz-protected amine products were isolated in high yield from reactions with a wide range of Z allylic ethers. A mechanism of the allylic substitution consistent with the results of the kinetics and kinetic isotope effect studies was proposed.

SUBMITTER: Lalic G 

PROVIDER: S-EPMC2528547 | biostudies-literature | 2005 Dec

REPOSITORIES: biostudies-literature

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Zirconium-mediated SN2' substitution of allylic ethers: regio- and stereospecific formation of protected allylic amines.

Lalic Gojko G   Blum Suzanne A SA   Bergman Robert G RG  

Journal of the American Chemical Society 20051201 48

A new zirconium-mediated, regio- and stereospecific SN2' substitution of allylic ethers with a nitrogen nucleophile has been developed. Cbz-protected amine products were isolated in high yield from reactions with a wide range of Z allylic ethers. A mechanism of the allylic substitution consistent with the results of the kinetics and kinetic isotope effect studies was proposed. ...[more]

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