Keto Furanylidene Building Blocks from Silyl Ethers of Monoalkynylated β- Keto Carbonyls with Iron(III) Chloride Hexahydrate-Iodine

Brittany Garner; Kristina Deveaux; Laura Gessner; Julia Trossarello; Shuting Dai; James W. Morgan; Karelle Aiken

doi:10.1515/hc-2012-0069

Keto Furanylidene Building Blocks from Silyl Ethers of Monoalkynylated β- Keto Carbonyls with Iron(III) Chloride Hexahydrate-Iodine

Brittany Garner, Kristina Deveaux, Laura Gessner, Julia Trossarello, Shuting Dai, James W. Morgan, Karelle Aiken

Biochemistry, Chemistry, & Physics

Georgia Southern University

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

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 hexahydrateiodine 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.

Original language	American English
Journal	Heterocyclic Communications
Volume	18
DOIs	https://doi.org/10.1515/hc-2012-0069
State	Published - Jan 1 2012

Keywords

(E)-diastereoselectivity
Deiodination
Furanylidene
Iodohydration

DC Disciplines

Chemistry
Organic Chemistry

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http://dx.doi.org/10.1515/hc-2012-0069

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title = "Keto Furanylidene Building Blocks from Silyl Ethers of Monoalkynylated β- Keto Carbonyls with Iron(III) Chloride Hexahydrate-Iodine",

abstract = "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 hexahydrateiodine 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.",

keywords = "(E)-diastereoselectivity, Deiodination, Furanylidene, Iodohydration",

author = "Brittany Garner and Kristina Deveaux and Laura Gessner and Julia Trossarello and Shuting Dai and Morgan, {James W.} and Karelle Aiken",

year = "2012",

month = jan,

day = "1",

doi = "10.1515/hc-2012-0069",

language = "American English",

volume = "18",

journal = "Heterocyclic Communications",

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TY - JOUR

T1 - Keto Furanylidene Building Blocks from Silyl Ethers of Monoalkynylated β- Keto Carbonyls with Iron(III) Chloride Hexahydrate-Iodine

AU - Garner, Brittany

AU - Deveaux, Kristina

AU - Gessner, Laura

AU - Trossarello, Julia

AU - Dai, Shuting

AU - Morgan, James W.

AU - Aiken, Karelle

PY - 2012/1/1

Y1 - 2012/1/1

N2 - 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 hexahydrateiodine 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.

AB - 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 hexahydrateiodine 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.

KW - (E)-diastereoselectivity

KW - Deiodination

KW - Furanylidene

KW - Iodohydration

UR - https://digitalcommons.georgiasouthern.edu/chem-facpubs/4

UR - http://dx.doi.org/10.1515/hc-2012-0069

U2 - 10.1515/hc-2012-0069

DO - 10.1515/hc-2012-0069

M3 - Article

SN - 0793-0283

VL - 18

JO - Heterocyclic Communications

JF - Heterocyclic Communications

ER -

Keto Furanylidene Building Blocks from Silyl Ethers of Monoalkynylated β- Keto Carbonyls with Iron(III) Chloride Hexahydrate-Iodine

Abstract

Keywords

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