(2R,3R)-3-[(1R)-1-{[tert-Butyl(dimethyl)silyl]oxy}ethyl]-4-oxoazetidin-2-yl Acetate in Zinc- and Samarium-Promoted Substitution Reactions with Methyl 2-Bromopropanoate and Methyl (2-Bromomethyl)prop-2-enoate. Unusual Cleavage of the N1‒C4 Bond in Azetidin-2-one Derivative with Migration of Methoxycarbonyl Group in Synthetic Approaches to Carbapenems and Their Analogs
- Авторы: Valiullina Z.R.1, Khasanova L.S.1, Selezneva N.K.1, Spirikhin L.V.1, Belokon’ Y.N.2, Miftakhov M.S.1
-
Учреждения:
- Institute of Organic Chemistry, Ufa Research Center
- Nesmeyanov Institute of Organoelement Compounds
- Выпуск: Том 54, № 7 (2018)
- Страницы: 1023-1030
- Раздел: Article
- URL: https://bakhtiniada.ru/1070-4280/article/view/218341
- DOI: https://doi.org/10.1134/S1070428018070096
- ID: 218341
Цитировать
Аннотация
The use of zinc in Barbier-type reactions of (2R,3R)-3-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-ethyl]-4-oxoazetidin-2-yl acetates with halogen derivatives led to the formation of expected substitution products. The reaction of the title compound with a reagent prepared from samarium powder, a catalytic amount of iodine, and methyl 2-bromopropanoate in THF gave an anomalous substitution product, methyl 2-{(2S,3S)-3-[(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl]-4-oxoazetidin-2-yl}-2(R,S)-methyl-3-oxopentanoate. Alkylation of the latter with methyl bromoacetate afforded methyl 2-{(2S,3S)-3-[(1R)-1-{[tert-butyl(dimethyl) silyl]oxy}ethyl]-1-(2-methoxy-2-oxoethyl)-4-oxoazetidin-2-yl}-2(RS)-methyl-3-oxopentanoate which underwent fragmentation through cleavage of the N1–C4 bond under the action of sodium bis(trimethylsilyl)-amide in THF at–78°C. The resulting acyclic amide, dimethyl {(2R,S,3Z)-2-[(1R)-1-{[tert-butyl(dimethyl)-silyl]oxy}ethyl)]-4-methyl-5-oxohept-3-enoylamino}malonate, was smoothly converted to new functionalized N-substituted pyrrolidinones via intramolecular Michael type cyclization in methylene chloride in the presence of NEt3–DMAP–Boc2O.
Об авторах
Z. Valiullina
Institute of Organic Chemistry, Ufa Research Center
Email: bioreg@anrb.ru
Россия, pr. Oktyabrya 71, Ufa Bashkortostan, 450054
L. Khasanova
Institute of Organic Chemistry, Ufa Research Center
Email: bioreg@anrb.ru
Россия, pr. Oktyabrya 71, Ufa Bashkortostan, 450054
N. Selezneva
Institute of Organic Chemistry, Ufa Research Center
Email: bioreg@anrb.ru
Россия, pr. Oktyabrya 71, Ufa Bashkortostan, 450054
L. Spirikhin
Institute of Organic Chemistry, Ufa Research Center
Email: bioreg@anrb.ru
Россия, pr. Oktyabrya 71, Ufa Bashkortostan, 450054
Yu. Belokon’
Nesmeyanov Institute of Organoelement Compounds
Email: bioreg@anrb.ru
Россия, ul. Vavilova 28, Moscow, 119991
M. Miftakhov
Institute of Organic Chemistry, Ufa Research Center
Автор, ответственный за переписку.
Email: bioreg@anrb.ru
Россия, pr. Oktyabrya 71, Ufa Bashkortostan, 450054
Дополнительные файлы
