有機触媒と自動循環反応

概要

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5-Deazaflavins and related compounds have been found to act as organic catalysts for the autorecycling oxidations of alcohols and amines to yield the corresponding carbonyl compounds in more than 100% yields. In particular, the pyridodipyrimidine derivatives (including bis-pyridodipyrimidines), which are structurally cyclized compounds of the amino analogues of Hantzsch esters and have a conjugated system similar to that of 5-deazaflavins, have shown outstanding oxidizing power toward a variety of alcohols to give the corresponding carbonyl compounds in astronomical yields based on the catalysts. On the other hand, it was found that 1,5-dihydro-5-deazaflavins are able to reduce carbonyl compounds to the corresponding alcohols in stoichiometric yield in the presence of strong proton sources and that these reductions are automatically recycled in formic acid. The autorecycling reduction was further developed into the synthesis of α-amino acids and the selective reduction of α, β-unsaturated carbonyl compounds. The syntheses of several kinds of organic catalysts were included additionally in this review. The conception of autorecycling reactions by organic catalysts would be very significant from the viewpoints of resource saving and environmental preservation as well as synthetic organic chemistry.
公益社団法人日本薬学会の論文
1984-02-25