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Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates
Journal article   Peer reviewed

Catalytic asymmetric oxidative couplings of 2-naphthols by tridentate N-ketopinidene-based vanadyl dicarboxylates

Nivrutti B. Barhate and Chien-Tien Chen
Organic Letters, Vol.4(15), pp.2529-2532
25/07/2002

Abstract

(Matrix presented) 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 CCl 4 . 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%.

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