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Asymmetric synthesis of chiral amines via nucleophilic addition to ferrocenylalkyl substituted imines

Journal Article


Abstract


  • The isomerically pure imine (Ia) formed from 1-ferrocenylethyl amine and benzaldehyde undergoes diastereoselective nucleophilic attack (Me-, D-) on the NC double bond to give ca. 67 33 mixtures of diastereomeric amines. The stereochemical outcome can be rationalised in terms of nucleophilic attack on the conformation of Ia in which allylic 1,3-strain is minimised. The opposite stereochemistry is favoured in the reduction by hydride of the related imine (Ib) formed from 1-ferrocenylethyl amine and methylphenyl ketone. These processes provide a useful new method for the asymmetric synthesis of amines from which the chiral ferrocenyl auxiliary may be readily regenerated. © 1990.

Publication Date


  • 1990

Citation


  • David, D. M., Kane-Maguire, L. A. P., & Pyne, S. G. (1990). Asymmetric synthesis of chiral amines via nucleophilic addition to ferrocenylalkyl substituted imines. Journal of Organometallic Chemistry, 390(1), c6. doi:10.1016/0022-328X(90)85090-L

Scopus Eid


  • 2-s2.0-4244177676

Web Of Science Accession Number


Start Page


  • c6

Volume


  • 390

Issue


  • 1

Abstract


  • The isomerically pure imine (Ia) formed from 1-ferrocenylethyl amine and benzaldehyde undergoes diastereoselective nucleophilic attack (Me-, D-) on the NC double bond to give ca. 67 33 mixtures of diastereomeric amines. The stereochemical outcome can be rationalised in terms of nucleophilic attack on the conformation of Ia in which allylic 1,3-strain is minimised. The opposite stereochemistry is favoured in the reduction by hydride of the related imine (Ib) formed from 1-ferrocenylethyl amine and methylphenyl ketone. These processes provide a useful new method for the asymmetric synthesis of amines from which the chiral ferrocenyl auxiliary may be readily regenerated. © 1990.

Publication Date


  • 1990

Citation


  • David, D. M., Kane-Maguire, L. A. P., & Pyne, S. G. (1990). Asymmetric synthesis of chiral amines via nucleophilic addition to ferrocenylalkyl substituted imines. Journal of Organometallic Chemistry, 390(1), c6. doi:10.1016/0022-328X(90)85090-L

Scopus Eid


  • 2-s2.0-4244177676

Web Of Science Accession Number


Start Page


  • c6

Volume


  • 390

Issue


  • 1