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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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Submitted
30 Apr 2018
Accepted
16 Jun 2018
First published
18 Jun 2018

Org. Biomol. Chem., 2018,16, 5551-5565
Article type
Review Article

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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