Catalytic Asymmetric Oxidative Couplings of 2-Naphthols by Tridentate N-Ketopinidene-Based Vanadyl Dicarboxylates
- 26 June 2002
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 4 (15) , 2529-2532
- https://doi.org/10.1021/ol026156g
Abstract
A series of oxovanadium(IV) complexes derived from tridentate N-ketopinidene-α-amino acids were synthesized. They serve as efficient catalysts for the enantioselective oxidative couplings of various 3-, 6-, or 7-substituted 2-naphthols. The best scenario involves the use of a vanadyl complex arising from l-tert-leucine in CCl4. The asymmetric couplings of 2-naphthols can be conducted smoothly at 40−45 °C under a stream of gaseous oxygen, leading to 2,2‘-dihydroxy-1,1‘-binaphthyls in good yields (61−99%) and with enantioselectivities of up to 87%.Keywords
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