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Design and synthesis of novel chiral dirhodium(II) carboxylate complexes for asymmetric cyclopropanation reactions

Citation

Adly, FG and Gardiner, MG and Ghanem, A, Design and synthesis of novel chiral dirhodium(II) carboxylate complexes for asymmetric cyclopropanation reactions, Chemistry: A European Journal, 22, (10) pp. 3447-3461. ISSN 0947-6539 (2016) [Refereed Article]

Copyright Statement

Copyright 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

DOI: doi:10.1002/chem.201504817

Abstract

A novel approach to the design of dirhodium(II) tetracarboxylates derived from (S)-amino acid ligands is reported. The approach is founded on tailoring the steric influences of the overall catalyst structure by reducing the local symmetry of the ligand's N-heterocyclic tether. The application of the new approach has led to the uncovering of [Rh2(S-tertPTTL)4] as a new member of the dirhodium(II) family with extraordinary selectivity in cyclopropanation reactions. The stereoselectivity of [Rh2(S-tertPTTL)4] was found to be comparable to that of [Rh2(S-PTAD)4] (up to >99 % ee), with the extra benefit of being more synthetically accessible. Correlations based on X-ray structures to justify the observed enantioinduction are also discussed.

Item Details

Item Type:Refereed Article
Keywords:catalysis, organometallic
Research Division:Chemical Sciences
Research Group:Inorganic Chemistry
Research Field:Transition Metal Chemistry
Objective Division:Manufacturing
Objective Group:Industrial Chemicals and Related Products
Objective Field:Organic Industrial Chemicals (excl. Resins, Rubber and Plastics)
Author:Gardiner, MG (Associate Professor Michael Gardiner)
ID Code:107801
Year Published:2016
Web of Science® Times Cited:13
Deposited By:Chemistry
Deposited On:2016-03-24
Last Modified:2017-11-02
Downloads:0

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