Abstract:
(2R,3R)-N-(3-Methoxy-2,3-dioxopropyl)-N-(4-methoxy-phenyl)-2,3-epoxybutanamide on treatment with strong bases (LDA, LHMDS) gives 3-[(1R)-1-hydroxyethyl]azetidin-2-one derivative, while the N-(3-methoxy-2-methylidene-3-oxo-propyl) analogue undergoes fragmentation.
Citation:
N. K. Selezneva, Z. R. Valiullina, L. S. Khasanova, F. A. Gimalova, R. Z. Biglova, M. S. Miftakhov, “Novel azetidinones for carbapenems and fragmentation in the allylamine precursor analogue”, Mendeleev Commun., 28:2 (2018), 131–132
Linking options:
https://www.mathnet.ru/eng/mendc1687
https://www.mathnet.ru/eng/mendc/v28/i2/p131
This publication is cited in the following 4 articles:
N. K Selezneva, A. M Galeeva, Z. R Valiullina, M. S Miftakhov, “Synthesis of (3S,4S)-4-Acetyl-3-(1R)-1-hydroxyethyl1-(4-methoxyphenyl)azetidin-2-one”, Žurnal organičeskoj himii, 59:1 (2023), 128
N. K. Selezneva, A. M. Galeeva, Z. R. Valiullina, M. S. Miftakhov, “Synthesis of (3S,4S)-4-Acetyl-3-(1R)-1-hydroxyethyl-1-(4-methoxyphenyl)azetidin-2-one”, Russ J Org Chem, 58:11 (2022), 1676
Josefa Anaya, Ramón M. Sánchez, Progress in Heterocyclic Chemistry, 31, 2020, 143
N. K. Selezneva, A. M. Galeeva, L. M. Khalilov, Z. R. Valiullina, M. S. Miftakhov, “Base-determinant chemodivergent transformations of chiral 2,3-dibromopropanamide derivative”, Mendeleev Commun., 30:3 (2020), 313–314
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