Journal
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY
Volume 39, Issue 7, Pages 1042-1047Publisher
MAIK NAUKA/INTERPERIODICA
DOI: 10.1023/B:RUJO.0000003201.57627.ee
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New chiral diaza crown ethers with exocyclic hydroxy groups were synthesized by reactions of (2S,3S)-1,4-dibenzyloxy-2,3-bis(2-oxiranylmethoxy)butane with N,N'-dibenzyl-1,2-ethanediamine and (4S,5S)-4,5-bis(benzylaminomethyl)-2,2-dimethyl-1,3-dioxolane. Catalytic debenzylation of the products gave the corresponding derivatives having secondary amino groups. The obtained diaza crown ethers, as well as some known crown ethers, were used as asymmetric catalysts in the reduction of pinacolone and acetophenone with sodium tetrahydridoborate in methylene chloride. Depending on the catalyst structure, the optical yield of the reduction products ranged from 5 to 90%.
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