Practical Stereoselective Syntheses of All Four ( 2 - Ethyl - 1 - aminocyclopropane - 1 - carboxylic acid )
نویسندگان
چکیده
All four stereoisomers of coronamic acid were synthesized from both enantiomers of 1,2-butanediol. Cyclopropanation of cyclic sulfate with the dibenzyl malonate' anion gaye cyclopropane dibenzyl ester in a quantitatiye ield. Transformation into a protected amino acid was achieyed by stereoselectiye hydrolysis and Cunius rearrangement as the key steps. Saponification and subsequent acidic hydrolysis in one pot and ion exchange gave a free amino acid in a high yield.
منابع مشابه
Synthesis of Deuterium - labeled 1 - Aminocyclopropane - 1 - carboxylic Acid
[ ZH2 IACC) ; 1-amino [ 2R, 3E-2H2] cyc lopropaneIcar boxy 1 ic acid (trans-[zH2]ACC) : and l-amino[2,2.3.3-~H~]cyclopropane1-carboxylic acid are described. The [2,2-2H2]and [2,2,3.3-2H4]ACC compounds were prepared from the appropriately deuterated 2-bromoethanol 4-methylbenzenesulfonates by reaction with ethyl isocyanoacetate and two moles oE sodium hydride. The transr2H2]ACC and &[2H2]ACC wer...
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