Alkynyltrifluoroborates as Versatile Tools in Organic Synthesis:  A New Route to Spiroketals

A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl α-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroke...

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Bibliographic Details
Published inOrganic letters Vol. 6; no. 26; pp. 4909 - 4911
Main Authors Doubský, Jan, Streinz, Ludvík, Šaman, David, Zedník, Jiří, Koutek, Bohumír
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 23.12.2004
Amer Chemical Soc
Subjects
Boron Compounds - chemistry
Catalysis
Chemistry
Chemistry, Organic
Cyclization
Lithium - chemistry
Molecular Structure
Palladium - chemistry
Physical Sciences
Science & Technology
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
SPIROACETAL
PHEROMONE
ACID-CHLORIDES
LACTONES
ALPHA,BETA-ACETYLENIC KETONES
STEREOCHEMISTRY
ALKYNYL KETONES
CONVENIENT
INSECT
ACETYLIDE
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Summary:A simple and efficient two-step approach to spiroketals is described. Key steps include the preparation of functionalized hydroxyl α-alkynones by ring-opening reactions of lactones with lithium alkynyltrifluoroborates followed by a palladium-catalyzed hydrogenation/spirocyclization of the prespiroketal intermediate.
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ISSN:1523-7060
1523-7052
DOI:10.1021/ol047987k