Formal [4 + 1]-Cycloaddition of Homopropargyl Alcohols to Diazo Dicarbonyl Compounds Giving Substituted Tetrahydrofurans

Formal [4 + 1]-Cycloaddition of Homopropargyl Alcohols to Diazo Dicarbonyl Compounds Giving Substituted Tetrahydrofurans

A novel formal [4 + 1]-cycloaddition of readily available homopropargyl alcohols with diazo dicarbonyl compounds is described, which involves tandem O–H insertion/Conia-ene cyclization under cooperative Rh(II)/Zn(II) catalysis. This reaction provides easy access to various substituted tetra­hydro­fu...

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Veröffentlicht in:Organic letters 2014-02, Vol.16 (3), p.1004-1007
Hauptverfasser: Urabe, Fumiya, Miyamoto, Shohei, Takahashi, Keisuke, Ishihara, Jun, Hatakeyama, Susumi
Format: Artikel
Sprache:eng
Schlagworte:
Alcohols - chemistry
Azo Compounds - chemical synthesis
Azo Compounds - chemistry
Catalysis
Cycloaddition Reaction
Furans - chemistry
Molecular Structure
Pargyline - analogs & derivatives
Pargyline - chemistry
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Zusammenfassung:A novel formal [4 + 1]-cycloaddition of readily available homopropargyl alcohols with diazo dicarbonyl compounds is described, which involves tandem O–H insertion/Conia-ene cyclization under cooperative Rh(II)/Zn(II) catalysis. This reaction provides easy access to various substituted tetra­hydro­furans and exhibits complete E-selectivity in the case of nonterminal alkynes.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol403746r