Nickel-catalyzed asymmetric allylation of alkyl Grignard reagents, effect of ligands, leaving groups and a kinetic resolution with a hard nucleophile

Tetrahedron Letters

Volumn 38, Issue 10, 1997, Pages 1713-1716

  Nomura, Nobuyoshi ^a   RajanBabu, T V ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; REAGENT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; ENANTIOMER; METHYLATION; SYNTHESIS;

EID: 0031562395     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00178-0     Document Type: Article

References (27)

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16. 6. While our study was in progress, Hoveyda reported nickel-catalyzed addition of alkyl Grignard reagents to allylic methyl ethers assisted by a properly positioned Lewis base in the molecule. Didiuk, M. T.; Morken, J. P.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 7273.
17. 2i were also found to be ineffective in the Ni-chemistry using methyl 1,3-diphenylallyl ether as a substrate.
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26. 15. For an example of a kinetic resolution in the case of Pd-mediated allylation see: Hayashi, T.; Yamamoto, A.; Ito, Y. J. Chem. Soc., Chem. Commun. 1986, 1090. For a successful Zr-catalyzed kinetic resolution of cyclic allyl ethers see: Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779.
27. 15. For an example of a kinetic resolution in the case of Pd-mediated allylation see: Hayashi, T.; Yamamoto, A.; Ito, Y. J. Chem. Soc., Chem. Commun. 1986, 1090. For a successful Zr-catalyzed kinetic resolution of cyclic allyl ethers see: Visser, M. S.; Harrity, J. P. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1996, 118, 3779.