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Asymmetric Synthesis via Heterocyclic Intermediates, XLVIII. Asymmetric Synthesis of Diastereomerically and Enantiomerically Pure, 3‐Substituted (2 S ,3 R )‐ N ‐Methylserine Esters
Author(s) -
Beulshausen Tessa,
Groth Ulrich,
Schöllkopf Ulrich
Publication year - 1992
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.199219920190
Subject(s) - chemistry , enantioselective synthesis , stereochemistry , organic chemistry , catalysis
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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