ChemInform Abstract: Control of Chemoselectivity in Dirhodium(II)-Catalyzed Reaction of 5,6-Dioxygenated 2-Diazo-3-oxohexanoates: C-H Insertion Reaction versus Oxonium Ylide Formation

Autor:	Toyoshige Kurata, Masazumi Ikeda, Akiharu Ueki, Yukiko Morioka, Takayuki Yakura, Kenji Tanaka
Rok vydání:	2010
Předmět:	chemistry.chemical_classification General Medicine Medicinal chemistry Catalysis chemistry.chemical_compound chemistry Ylide Insertion reaction Boiling Organic chemistry Diazo Chemoselectivity Oxonium ion Dichloromethane
Zdroj:	ChemInform. 29
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.199852059
Popis:	Methyl (S)-2-diazo-4-(3, 3-dimethyl-2, 4-dioxolan-1-yl)-3-oxobutanoate (1), upon treatment with Rh2(OAc)4 in boiling dichloromethane, gave methyl (1S, 5S)-2, 2-dimethyl-7-oxo-3, 8-dioxabicyclo[3.2.1]octane-1-carboxylate (2) via oxonium ylide formation/1, 2-shift. On the other hand, similar treatment of methyl (S)-5, 6-bis(tert-butyldimethylsilyloxy)-2-diazo-3-oxohexanoate (3a) gave methyl 3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-carboxylate (4a) via the C-H insertion reaction.
Databáze:	OpenAIRE
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