Synthesis of Multi-Substituted Cyclobutanes and Alkylidenecyclobutanes by the Reaction of Cyclobutylmagnesium Carbenoids with Nucleophiles

Autor:	Masashi Ishigaki, Tsuyoshi Satoh, Nobuhito Nakaya, Toshifumi Miyagawa, Takashi Kasuya, Shimpei Sugiyama, Mio Inumaru
Rok vydání:	2011
Předmět:	Cyclobutanes Magnesium Organic Chemistry chemistry.chemical_element Medicinal chemistry Chloride Catalysis Cyclobutane chemistry.chemical_compound Nucleophile chemistry Reagent medicine Lithium medicine.drug Carbanion
Zdroj:	Synthesis. 2011:397-408
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0030-1258391
Popis:	Treatment of 1-chlorocyclobutyl p-tolyl sulfoxides with Grignard reagents such as ethylmagnesium chloride, isopropylmagnesium chloride, and cyclopentylmagnesium chloride in THF at low temperature gave cyclobutylmagnesium carbenoids in high yields. The generated magnesium carbenoids were found to be stable at -78 ˚C for at least 30 minutes. The cyclobutylmagnesium carbenoids reacted with several nucleophiles to give multi-substituted cyclobutanes. The reaction of the cyclobutylmagnesium carbenoids with lithium α-sulfonyl carbanions afforded alkylidenecyclobutanes in moderate to good yields.
Databáze:	OpenAIRE
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