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  • Title: Enantioselective aerobic oxidation of α-hydroxy-ketones catalyzed by oxidovanadium(V) methoxides bearing chiral, N-salicylidene-tert-butylglycinates.
    Author: Chen CT, Kao JQ, Salunke SB, Lin YH.
    Journal: Org Lett; 2011 Jan 07; 13(1):26-9. PubMed ID: 21121619.
    Abstract:
    Chiral oxidovanadium(V) methoxides prepared from 3,5-disubstituted-N-salicylidene-l-tert-butylglycines and vanadyl sulfate in air-saturated MeOH serve as highly enantioselective catalysts for asymmetric aerobic oxidations and kinetic resolution of alkyl, aryl, and heteroaryl α-hydroxy-ketones with differed α-substituents at ambient temperature in toluene or TBME (tert-butyl methyl ether). The best scenarios involve the use of complexes which bear the tridendate templates derived from 3,5-diphenyl- or 3-o-biphenyl-5-nitro-salicyaldehyde. The kinetic resolution selectivities of the aerobic oxidation process are in the range of 12 to >1000 based on the selectivity factors (k(rel)).
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