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Issue 31, 2018
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Dibenzofuran-4,6-bis(oxazoline) (DBFOX). A novel trans-chelating bis(oxazoline) ligand for asymmetric reactions

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Abstract

The trans-chelating bis(oxazoline) ligand (R,R)-4,6-dibenzofurandiyl-2,2′-bis(4-phenyloxazoline) [(R,R)-DBFOX/Ph] coordinates metal ions to give C2-symmetric complexes which effectively catalyze a variety of asymmetric reactions. (R,R)-DBFOX/Ph·Ni(ClO4)2·3H2O, whose crystal structure is octahedral with three aqua ligands, can be stored under air for several months without loss of catalytic activity and promotes highly enantioselective reactions even in the presence of excess amounts of water, alcohols, amines, and acids. The complex shows remarkable chiral amplification in asymmetric Diels–Alder (DA) reactions. This review focuses on enantioselective reactions catalyzed by (R,R)-DBFOX/Ph·metal complexes.

Graphical abstract: Dibenzofuran-4,6-bis(oxazoline) (DBFOX). A novel trans-chelating bis(oxazoline) ligand for asymmetric reactions

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Publication details

The article was received on 30 Apr 2018, accepted on 16 Jun 2018 and first published on 18 Jun 2018


Article type: Review Article
DOI: 10.1039/C8OB01010B
Citation: Org. Biomol. Chem., 2018,16, 5551-5565
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    Dibenzofuran-4,6-bis(oxazoline) (DBFOX). A novel trans-chelating bis(oxazoline) ligand for asymmetric reactions

    K. Itoh and M. P. Sibi, Org. Biomol. Chem., 2018, 16, 5551
    DOI: 10.1039/C8OB01010B

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