Preparation of Tetrasubstituted Furans via Intramolecular Wittig Reactions with Phosphorus Ylides as Intermediates

Novel preparation of tetrasubstituted furans, starting from the Michael acceptors, tributylphosphine, and acyl chlorides, is realized. A broad range of highly functional furans can be efficiently generated in one step at room temperature within 10 min to 21 h in moderate to high yields (60−99%). The...

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Published inOrganic letters Vol. 12; no. 13; pp. 3066 - 3069
Main Authors Kao, Tzu-Ting, Syu, Siang-en, Jhang, Yi-Wun, Lin, Wenwei
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.07.2010
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Furans - chemical synthesis
Furans - chemistry
Molecular Structure
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
NUCLEOPHILES
2-(1-ALKYNYL)-2-ALKEN-1-ONES
HETEROCYCLES
MECHANISM
POLYSUBSTITUTED FURANS
MODULAR ENTRY
ALLENYL KETONES
SUBSTITUTED FURANS
CYCLIZATION
REGIOCONTROLLED SYNTHESIS
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Summary:Novel preparation of tetrasubstituted furans, starting from the Michael acceptors, tributylphosphine, and acyl chlorides, is realized. A broad range of highly functional furans can be efficiently generated in one step at room temperature within 10 min to 21 h in moderate to high yields (60−99%). The reaction was proposed to proceed via intramolecular Wittig-type reactions, using phosphorus ylides as intermediates.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/ol101080q