Synthesis of naturally occurring (2S,3S)-(+)-aziridine-2,3-dicarboxylic acid.
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Add time:08/14/2019 Source:sciencedirect.com
Diethyl (2R,3R)-(−)-oxirane-2,3-dicarboxylate was converted into diethyl (2S,3S)-(+)-aziridine-2,3-dicarboxylate in two steps, viz. ring opening with trimethylsilyl azide in N,N-dimethylformamide containing one equivalent of ethanol, followed by treatment with triphenylphosphine in N,N-dimethylformamide. Subsequent hydrolysis with lithium hydroxide and acidification with Dowex 50W-X2 (H+) afforded (2S,3S)-(+)-aziridine-2,3-dicarboxylic acid, which was identical in all respects to the natural product.
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