Bi[5,5-bis(hydroxymethyl)-3-methyl-2-oxomorpholin-3-yl] (BHM-3 dimer). A low toxicity, water-soluble, one-electron reducing agent

Free-Radical Reactions in the Synthesis of α-Amino Acids and Derivatives

“…A range of dimers has been obtained, including the diol 230 which has been designed to be soluble in water. , In a variation of the dimerization procedure, the bis(oxazinone) 231 was used to make macrocycles with coronand structure . The radicals formed by bond homolysis of the dimers act as one electron reducing agents, reflecting the ease of electron transfer from α-carbon-centered amino acid radicals, referred to above.…”

“…The radicals formed by bond homolysis of the dimers act as one electron reducing agents, reflecting the ease of electron transfer from α-carbon-centered amino acid radicals, referred to above. Reductions by the dimers of compounds such as adriamycin and daunomycin have been studied in detail, as models for the in vivo manipulation of quinone antitumor drugs. ,,,−

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“…Reductions by the dimers of compounds such as adriamycin and daunomycin have been studied in detail, as models for the in vivo manipulation of quinone antitumor drugs. 240,245,246,[248][249][250][251][252][253][254][255][256][257][258] As a final example of the production of amino acid radicals through functional group transformations, photolysis of the pyrazolines 232a-c gave the corresponding cyclopropylamino acid derivatives 234a-…”

Photoinduced Formation of β-Oxy-α,α-disubstituted-α-amino Acid Derivatives from Ketoximes

“…The success of the above reactions is in part ascribed to the stability of the starting α-alkoxycarbonyl ketoxime ethers 5a − c under the reaction conditions. , Remarkably, they tolerate easily abstracted hydrogen atoms on the starting ketoximes 5 , in particular the benzylic hydrogens of the oxime ether group.…”