Chiral auxiliary based approach toward the synthesis of C-glycosylated amino acids.
[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.
Westermann
B
B
Universität Paderborn, Fachbereich für Chemie und Chemietechnik, Warburgerstr. 100, 33098 Paderborn, Germany. bw@fb13n.uni-paderborn.de
Walter
A
A
Flörke
U
U
Altenbach
H J
HJ
D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D004612:Elliptocytosis, Hereditary; D005998:Glycine / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008610:Menthol; D015394:Molecular Structure; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000737:chemistry
D000596:Amino Acids; D006027:Glycosides; D013729:Terpenes; D008610:Menthol; C019466:menthone; D005998:Glycine