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Issue 5, 2019
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Iron-catalyzed asymmetric intramolecular cyclopropanation reactions using chiral tetramethyl-1,1′-spirobiindane-based bisoxazoline (TMSI-BOX) ligands

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Abstract

The versatile application of chiral bisoxazoline (BOX) ligands in diverse metal-catalyzed asymmetric reactions results in growing demand for novel BOX ligands containing different motifs. Herein, the successful development of a chiral spiro bisoxazoline ligand (TMSI-BOX) on the basis of the tetramethyl-1,1′-spirobiindane motif and bisoxazoline chelating units is described. The corresponding Fe complexes of TMSI-BOX proved to be excellent catalysts in the asymmetric intramolecular cyclopropanation reaction of diazo derivatives, providing synthetically versatile [3.1.0]bicycloalkane derivatives bearing two contiguous quaternary chiral centers with high enantiomeric purity.

Graphical abstract: Iron-catalyzed asymmetric intramolecular cyclopropanation reactions using chiral tetramethyl-1,1′-spirobiindane-based bisoxazoline (TMSI-BOX) ligands

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Supplementary files

Article information


Submitted
10 Dec 2018
Accepted
09 Jan 2019
First published
09 Jan 2019

Org. Biomol. Chem., 2019,17, 1154-1162
Article type
Paper

Iron-catalyzed asymmetric intramolecular cyclopropanation reactions using chiral tetramethyl-1,1′-spirobiindane-based bisoxazoline (TMSI-BOX) ligands

H. Gu, S. Huang and X. Lin, Org. Biomol. Chem., 2019, 17, 1154
DOI: 10.1039/C8OB03065K

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