2019
DOI: 10.1021/acs.orglett.8b03910
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Direct Synthesis of Free α-Amino Acids by Telescoping Three-Step Process from 1,2-Diols

Abstract: A practical telescoping three-step process for the syntheses of α-amino acids from the corresponding 1,2-diols has been developed. This process enables the direct synthesis of free α-amino acids without any protection/deprotection step. This method was also effective for the preparation of a 15N-labeled α-amino acid. 1,2-Diols bearing α,β-unsaturated ester moieties afforded bicyclic α-amino acids through intramolecular [3 + 2] cycloadditions. A preliminary study suggests that the resultant α-amino acids are re… Show more

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Cited by 9 publications
(1 citation statement)
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References 43 publications
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“…Another substantial species present was Unk3. HSQC and HMBC data revealed an amino acid backbone, however the side chain was revealed via COSY and TOCSY to be a simple ethyl group like homo-alanine (hAla) (Inada et al, 2019). Its presence could not be detected by LC-MS, so this metabolite remains unknown.…”
Section: Excretion Of Organic Compoundsmentioning
confidence: 99%
“…Another substantial species present was Unk3. HSQC and HMBC data revealed an amino acid backbone, however the side chain was revealed via COSY and TOCSY to be a simple ethyl group like homo-alanine (hAla) (Inada et al, 2019). Its presence could not be detected by LC-MS, so this metabolite remains unknown.…”
Section: Excretion Of Organic Compoundsmentioning
confidence: 99%