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Diastereoselective nucleophilic additions to imines attached to tricarbonyl(arene)chromium moieties

Journal Article


Abstract


  • A range of imine complexes has been prepared which possess planar chirality associated with the attached tricarbonyl(1,2-disubstituted arene)chromium moiety. Nucleophilic addition to the imine group of these complexes occurs with high diastereoselectivity, providing an efficient route to the asymmetric synthesis of chiral amines. The stereochemical outcome of the additions may be rationalized in terms of a favoured conformer for the complexes, with nucleophilic attack occurring on the face of the imine anti to the sterically demanding Cr(CO)3 group. Related studies have also been carried out on imine complexes in which the chiral auxiliary is instead a carbon centre attached to the imine N atom. In these latter systems high diastereoselectivity was also observed, but was not superior to that achieved with the related free amines.

Publication Date


  • 1994

Citation


  • David, D. M., Kane-Maguire, L. A. P., & Pyne, S. G. (1994). Diastereoselective nucleophilic additions to imines attached to tricarbonyl(arene)chromium moieties. Journal of the Chemical Society, Dalton Transactions, (3), 289-295. doi:10.1039/DT9940000289

Scopus Eid


  • 2-s2.0-37049075287

Web Of Science Accession Number


Start Page


  • 289

End Page


  • 295

Issue


  • 3

Abstract


  • A range of imine complexes has been prepared which possess planar chirality associated with the attached tricarbonyl(1,2-disubstituted arene)chromium moiety. Nucleophilic addition to the imine group of these complexes occurs with high diastereoselectivity, providing an efficient route to the asymmetric synthesis of chiral amines. The stereochemical outcome of the additions may be rationalized in terms of a favoured conformer for the complexes, with nucleophilic attack occurring on the face of the imine anti to the sterically demanding Cr(CO)3 group. Related studies have also been carried out on imine complexes in which the chiral auxiliary is instead a carbon centre attached to the imine N atom. In these latter systems high diastereoselectivity was also observed, but was not superior to that achieved with the related free amines.

Publication Date


  • 1994

Citation


  • David, D. M., Kane-Maguire, L. A. P., & Pyne, S. G. (1994). Diastereoselective nucleophilic additions to imines attached to tricarbonyl(arene)chromium moieties. Journal of the Chemical Society, Dalton Transactions, (3), 289-295. doi:10.1039/DT9940000289

Scopus Eid


  • 2-s2.0-37049075287

Web Of Science Accession Number


Start Page


  • 289

End Page


  • 295

Issue


  • 3