Design and Synthesis of Novel Chiral Dirhodium(II) Carboxylate Complexes for Asymmetric Cyclopropanation Reactions

Chemistry : a European Journal
Frady G AdlyAshraf Ghanem

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-(tert) PTTL)4 ] as a new member of the dirhodium(II) family with extraordinary selectivity in cyclopropanation reactions. The stereoselectivity of [Rh2 (S-(tert) PTTL)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.

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Citations

Feb 15, 2017·Journal of the American Chemical Society·Ji-Min YangQi-Lin Zhou
Jun 3, 2017·Chemical Communications : Chem Comm·Katharina J HockRene M Koenigs
Oct 7, 2016·Chemical Communications : Chem Comm·RahulKumar Rajmani SinghRai-Shung Liu
Jun 26, 2018·Chemical Science·Igor D Jurberg, Huw M L Davies
Apr 9, 2021·Journal of the American Chemical Society·Santanu SinghaAlois Fürstner
Aug 26, 2017·The Journal of Organic Chemistry·Mohammed H Al-HunitiMitchell P Croatt
Nov 25, 2017·The Journal of Organic Chemistry·Jessica G K O'BrienJoseph M Fox

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