Jump to main content
Jump to site search

Issue 21, 2003
Previous Article Next Article

Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc–aldehyde additions

Author affiliations

Abstract

The ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core D-glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions to aldehydes, with variations in ΔΔG(R-S) of up to 5650 J mol−1 that create opposing senses of asymmetric induction and that are consistent with models based on several ligand X-ray structures and molecular mechanics analysis. Factorial analysis of enantioselectivity using key dihedral angles and steric volume on N-2 also highlight the potential for the use of factorial design in ligand construction.

Graphical abstract: Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc–aldehyde additions

Back to tab navigation

Supplementary files

Additions and corrections

Publication details

The article was received on 12 Aug 2003, accepted on 18 Sep 2003 and first published on 07 Oct 2003


Article type: Paper
DOI: 10.1039/B309715N
Citation: Org. Biomol. Chem., 2003,1, 3826-3838
  •   Request permissions

    Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc–aldehyde additions

    D. P. G. Emmerson, R. Villard, C. Mugnaini, A. Batsanov, J. A. K. Howard, W. P. Hems, R. P. Tooze and B. G. Davis, Org. Biomol. Chem., 2003, 1, 3826
    DOI: 10.1039/B309715N

Search articles by author

Spotlight

Advertisements