Keto furanylidene building blocks from silyl ethers of monoalkynylated β-keto carbonyls with iron(III) chloride hexahydrate-iodine

Keto furanylidene building blocks are synthesized from the unique silyl ethers of monoalkynylated β-keto carbonyls. The procedure consists of a desilylation, cyclization, and alkyne hydration facilitated by either a one-pot reaction with iron(III) chloride hexahydrate-iodine or a two-step procedure...

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Published inHeterocyclic communications Vol. 18; no. 4; pp. 181 - 187
Main Authors Garner, Brittany, Deveaux, Kristina, Gessner, Laura, Trossarello, Julia, Dai, Shuting, Morgan, Whitney J., Aiken, Karelle S.
Format Journal Article
LanguageEnglish
Published De Gruyter 01.10.2012
Subjects
deiodination
diastereoselectivity
furanylidene
iodohydration
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Summary:Keto furanylidene building blocks are synthesized from the unique silyl ethers of monoalkynylated β-keto carbonyls. The procedure consists of a desilylation, cyclization, and alkyne hydration facilitated by either a one-pot reaction with iron(III) chloride hexahydrate-iodine or a two-step procedure with tosylic acid and gold(I) chloride. Notably, the hydration of the terminal alkyne with iron(III) chloride hexahydrate-iodine reagent is a safer and new alternative to the use of mercury(II) salts.
ISSN:0793-0283
2191-0197
DOI:10.1515/hc-2012-0069