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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Bibliographic Details
Published inOrganic letters Vol. 16; no. 3; pp. 1004 - 1007
Main Authors Urabe, Fumiya, Miyamoto, Shohei, Takahashi, Keisuke, Ishihara, Jun, Hatakeyama, Susumi
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 07.02.2014
Amer Chemical Soc
Subjects
Alcohols - chemistry
Azo Compounds - chemical synthesis
Azo Compounds - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cycloaddition Reaction
Furans - chemistry
Molecular Structure
Pargyline - analogs & derivatives
Pargyline - chemistry
Physical Sciences
Science & Technology
4+1 CYCLOADDITION
ADDITION-CYCLIZATION REACTIONS
BETA-KETOESTERS
COOPERATIVE CATALYSIS
ENANTIOSELECTIVE SYNTHESIS
ONE-POT SYNTHESIS
5-ENDO-DIG CARBOCYCLIZATION
STEREOSELECTIVE-SYNTHESIS
EFFICIENT
CONIA-ENE REACTION
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Summary: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.
Bibliography:KAKEN
ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol403746r