Catalytic Asymmetric Oxidative Couplings of 2-Naphthols by Tridentate N-Ketopinidene-Based Vanadyl Dicarboxylates
Organic Letters2002Vol. 4(15), pp. 2529–2532
Citations Over TimeTop 10% of 2002 papers
Abstract
[reaction: see text] A series of oxovanadium(IV) complexes derived from tridentate N-ketopinidene-alpha-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 degrees 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%.
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