93715-75-4Relevant academic research and scientific papers
Copper-Catalyzed Oxy-aminomethylation of Diazo Compounds with N, O-Acetals
Yu, Jianliang,Chen, Long,Sun, Jiangtao
supporting information, p. 1664 - 1667 (2019/03/11)
A novel oxy-aminomethylation reaction of diazo compounds has been developed, providing the α-hydroxy-β2-amino acid derivatives with quaternary carbon centers in moderate to excellent yields. Importantly, the readily available N,O-acetals have been employed as efficient bifunctionalization reagents to react with copper carbene intermediates, leading to the concurrent incorporation of an alkoxy and an iminium group into one molecule. Moreover, a water-involved three-component reaction occurs to deliver the free-hydroxy amino acid derivatives.
dl-Isoserine and Related Compounds
Williams, Theresa M.,Crumbie, Robyn,Mosher, Harry S.
, p. 91 - 97 (2007/10/02)
Syntheses of dl-isoserine (3-amino-2-hydroxypropanoic acid, 7) and further functionalized derivatives are described.Reaction of glyoxylic acid with nitromethane gives the known 2-hydroxy-3-nitropropanoic acid (8), which upon hydrogenolysis affords dl-isoserine in high yield.The comparable nitro-aldol reaction of 3-nitropropanal ethylene acetal (2) with glyoxylic acid produces 2-hydroxy-3-nitro-5-oxopentanoic acid ethylene acetal (4a) as a mixture of erythro and threo isomers.The methyl esters of hydroxy acid 4a are chromatographically separable as the tert-butyldimethysilyl ethers.Catalytic reduction (Pd/C) of these nitro compounds gives the corresponding methyl 3-amino-2-hydroxy-5-oxopentanoate ethylene acetals 9.Ethyl 2-hydroxy-3-phthalimidopropanoate (22) and ethyl 2-oxo-3-phthalimidopropanoate (23) were also prepared along with several other N-protected β-amino-α-oxy esters related to isoserine.
