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- W2126427098 abstract "A simple and high-yielding method for the preparation of cyclopropane amino acids is described. The novel method involves the one-pot cyclopropanation of readily available dehydroamino acids using aryl and unsaturated diazo compounds generated in situ from the corresponding tosylhydrazone salts. It was found that thermal 1,3-dipolar cycloaddition followed by nitrogen extrusion gave the cyclopropane amino acid derivatives with good E selectivity, while reactions in the presence of meso-tetraphenylporphyrin iron chloride gave predominantly the corresponding Z isomers. The synthetic utility of this process was demonstrated in the synthesis of (+/-)-(Z)-2,3-methanophenylalanine [(+/-)-(Z)-1], the anti-Parkinson (+/-)-(E)-2,3-methano-m-tyrosine [(+/-)-(E)-2], and the natural product (+/-)-coronamic acid [(+/-)-3]." @default.
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- W2126427098 date "2003-11-01" @default.
- W2126427098 modified "2023-10-12" @default.
- W2126427098 title "Diastereoselective Synthesis of Cyclopropane Amino Acids Using Diazo Compounds Generated in Situ" @default.
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- W2126427098 doi "https://doi.org/10.1021/jo035060c" @default.
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