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Asymmetric Synthesis via Heterocyclic Intermediates, XLVIII. Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure, 3-Substituted (2S,3R)-N-Methylserine Esters

✍ Scribed by Beulshausen, Tessa ;Groth, Ulrich ;Schöllkopf, Ulrich

Publisher: John Wiley and Sons
Year: 1992
Tongue: English
Weight: 398 KB
Volume: 1992
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199219920190

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✦ Synopsis

Abstract

A novel method for the synthesis of N‐methylserines has been developed. The oxazolidines 4 are formed by condensation of the serine methyl esters 1 with formaldehyde. These intermediates are subsequently reduced to the N‐methylserine methyl esters 9 by an acid‐catalyzed ring opening via their iminium ions 2 with triethylsilane/trifluoroacetic acid.

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