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Updated: Oct 7, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Chiral auxiliary based approach toward the synthesis of C-glycosylated amino acids
B Westermann1, A Walter, U Flörke
1Universität Paderborn, Fachbereich für Chemie und Chemietechnik, Warburgerstr. 100, 33098 Paderborn, Germany. bw@fb13n.uni-paderborn.de
Abstract:
[reaction in text] In a chiral auxiliary based method C-glycosylated amino acids can be obtained by a 1,3-dipolar cycloaddition of a chiral glycine equivalent and C-1 allyl- or vinyl-derived carbohydrate building blocks as the key step. The products are formed regio- and diastereoselectively. Reductive cleavage of the N-O bond of the isoxazolidine and of the chiral auxiliary leads to C-glycosylated amino acids. The use of (-)-menthone to (+)-menthone as the auxiliary leads to the corresponding diastereomers.
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