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Alkene hydroamination with a chiral zirconium catalyst. Connecting ligand design, precatalyst structure and reactivity trends

TitleAlkene hydroamination with a chiral zirconium catalyst. Connecting ligand design, precatalyst structure and reactivity trends
Publication TypeJournal Article
Year of Publication2014
AuthorsYonson, N, Yim, JC-H, Schafer, LL
JournalInorganica Chimica Acta
Volume422
Pagination14-20
Date PublishedOCT 1
ISSN0020-1693
Abstract

A set of chiral bis(amidate) proligands were synthesized based on a 3,3'-substituted biphenyldiamine backbone. Zirconium precatalysts were synthesized using these proligands in situ and used for catalytic testing for intramolecular alkene hydroamination, achieving moderate enantiomeric excesses. Ligands containing electron-withdrawing substituents were found to be exceptionally reactive, in some cases catalyzing formation of pyrrolidine products at room temperature. Substitution at the 3,3'-position of the biphenyldiamine backbone was observed to significantly impact N,O-chelate binding modes, which in turn affect observed enantioselectivities. (C) 2014 Elsevier B. V. All rights reserved.

DOI10.1016/j.ica.2014.07.073