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• W2017489079 abstract "[reaction: see text] A practical, large-scale synthesis of a beta-amino ester 1 was developed. A chiral imine derived from (S)-phenylglycinol and 3-trimethylsilylpropanal was coupled with the Reformatsky reagent 3 with high diastereoselectivity (de > 98%) to give (SS)-4a as the major isomer. The amino alcohol residue of the coupling product 4 was oxidatively cleaved with sodium periodate in the presence of methylamine. An unusual selective oxidative cleavage of the (SS)-isomer was observed and the imine 6 was obtained with ee > 99% while the (RS)-4b 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 1 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 beta-amino esters." @default.
• W2017489079 created "2016-06-24" @default.
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• W2017489079 date "2005-06-03" @default.
• W2017489079 modified "2023-09-24" @default.
• W2017489079 title "Practical Enantioselective Synthesis of β-Substituted-β-amino Esters" @default.
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• W2017489079 doi "https://doi.org/10.1021/jo050177h" @default.
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