Zirconium-mediated SN2' substitution of allylic ethers: regio- and stereospecific formation of protected allylic amines.
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.
Lalic
Gojko
G
Department of Chemistry, University of California, Berkeley, 94720, USA.
Blum
Suzanne A
SA
Bergman
Robert G
RG
D000475:Alkenes / Q000737:chemistry; D000498:Allyl Compounds / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D007700:Kinetics; D009942:Organometallic Compounds / Q000737:chemistry; D013237:Stereoisomerism; D015040:Zirconium / Q000737:chemistry*
D000475:Alkenes; D000498:Allyl Compounds; D000588:Amines; D004987:Ethers; D009942:Organometallic Compounds; D015040:Zirconium