IODINE ACETATE AS A MILD SELECTIVE AGENT FOR THE WAGNER–MEERWEIN REARRANGEMENT IN 3a,6-EPOXYISOINDOLES
Sign Up to like & getrecommendations! Published in 2020 at "Chemistry of Heterocyclic Compounds"
DOI: 10.1007/5713
Abstract: Изучена инициируемая иодом катионная скелетная перегруппировка Вагнера–Меервейна в ряду тетрагидро-3a,6-эпоксиизоиндол-1-онов. Показано, что под действием ацетата иода в среде уксусного ангидрида реакция протекает регио- и стереоселективно с образованием ацетатов 5-иод-4,6-эпоксициклопента[ c ]пиридин-4-ила. Предложенный реагент обеспечиваетлучшие выходы… read more here.
Keywords: wagner meerwein; iodine acetate; selective agent; mild selective ... See more keywords
Novel Sesquiterpenoid Skeletons by Wagner-Meerwein Rearrangements of Longipinane-9,13-diol-1-one Derivatives.
Sign Up to like & getrecommendations! Published in 2021 at "Journal of natural products"
DOI: 10.1021/acs.jnatprod.0c01160
Abstract: The partial or total hydrolysis of (3R,4S,5S,6S,9R,10R,11R)-9,13-diangeloyloxylongipinan-1-one (1), isolated from the roots of Stevia viscida, gave alcohols 2 or 3, respectively, which were subjected to molecular rearrangements with boron trifluoride etherate. Compound 2 afforded (3R,4R,5R,6S,9R,10S,11S)-11,13-oxyneomorelian-1-one… read more here.
Keywords: skeletons wagner; novel sesquiterpenoid; wagner meerwein; meerwein rearrangements ... See more keywords
Phosphorus-Involved Wagner-Meerwein Rearrangement of Phosphiranes: An Entry to Four-Membered Phosphacycles.
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DOI: 10.1021/acs.orglett.2c04052
Abstract: Phosphenium ions [R2P]+ are important and highly reactive dicoordinate phosphorus species. Herein, we report a rearrangement of the carbocation into the phosphenium cation driven by ring strain. This phosphorus-involved Wagner-Meerwein rearrangement pathway converted the 1-acylphosphirane… read more here.
Keywords: phosphorus involved; wagner meerwein; involved wagner; meerwein rearrangement ... See more keywords
Synthesis of Piperidinone and Azepanone Fused Indoles via a Wagner–Meerwein Type 1,2-Amide Migration of 2-Spiropseudoindoxyls
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DOI: 10.1055/s-0036-1588138
Abstract: Spiropseudoindoxyls were synthesized by using a gold(III)-catalyzed intramolecular nitroalkyne redox–dipolar cycloaddition cascade. These compounds were then transformed into novel piperidinone and azepanone fused indoles via a straightforward hydrogenation. The reaction mechanism of this ring expansion… read more here.
Keywords: wagner meerwein; piperidinone azepanone; meerwein type; indoles via ... See more keywords