Awasthi, Alok K. published the artcilePractical Enantioselective Synthesis of β-Substituted-β-amino Esters, Computed Properties of 19652-33-6, the publication is Journal of Organic Chemistry (2005), 70(14), 5387-5397, database is CAplus and MEDLINE.
A practical, large-scale synthesis of a β-amino ester was developed. A chiral imine derived from (S)-phenylglycinol and 3-trimethylsilylpropanal was coupled with a Reformatskii reagent with high diastereoselectivity (de > 98%) to give (3S)-3-[[(1S)-2-hydroxy-1-phenylethyl]amino]-5-(trimethylsilyl)-4-pentynoic acid 1,1-dimethylethyl ester (I) as the major isomer. The amino alc. residue of the coupling product I was oxidatively cleaved with sodium periodate in the presence of methylamine. An unusual selective oxidative cleavage of I was observed and an imine was obtained with ee >99% while (3R)-3-[[(1S)-2-hydroxy-1-phenylethyl]amino]-5-(trimethylsilyl)-4-pentynoic acid 1,1-dimethylethyl ester [(R,S)-isomer] was not cleaved. Reaction with p-toluenesulfonic acid monohydrate allowed for the hydrolysis of the imine and the isolation of the amine as its salt. The title compound was then obtained by transesterification, desilylation, and hydrochloride salt formation in a one-pot process. The method was successfully applied toward the synthesis of a wide variety of β-amino esters.
Journal of Organic Chemistry published new progress about 19652-33-6. 19652-33-6 belongs to chlorides-buliding-blocks, auxiliary class Chloride,Bromide,Benzene,Phenol,Aldehyde, name is 5-Bromo-3-chloro-2-hydroxybenzaldehyde, and the molecular formula is C7H4BrClO2, Computed Properties of 19652-33-6.
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