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Synthesis of fluorinated compounds b...

Pham, Kenny.

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Synthesis of fluorinated compounds by one-pot reactions and asymmetric organocatalysis.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Synthesis of fluorinated compounds by one-pot reactions and asymmetric organocatalysis./
作者:	Pham, Kenny.
出版者:	Ann Arbor : ProQuest Dissertations & Theses, : 2016,
面頁冊數:	214 p.
附註:	Source: Masters Abstracts International, Volume: 55-05.
Contained By:	Masters Abstracts International55-05(E).
標題:	Organic chemistry. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10118484
ISBN:	9781339798158

Synthesis of fluorinated compounds by one-pot reactions and asymmetric organocatalysis.
Pham, Kenny.

Synthesis of fluorinated compounds by one-pot reactions and asymmetric organocatalysis. - Ann Arbor : ProQuest Dissertations & Theses, 2016 - 214 p.

Source: Masters Abstracts International, Volume: 55-05.

Thesis (M.S.)--University of Massachusetts Boston, 2016.

The synthesis of organofluorine molecules has become increasingly important in medicinal and agricultural chemistry because fluorinated molecules usually have unique chemical and biological properties. Fluorination can be combined with other chemicals in one-pot synthesis to save reaction time and energy, and to reduce the amount of waste by eliminating the intermediate purification step. The first project discussed in this thesis is the fluorination of beta--keto carbonyl with Selectfluor(TM) followed by the Mannich reaction with anilines and benzaldehydes for the synthesis of alpha--fluoro and aminomethylated 1,3-dicarbonyl compounds.

ISBN: 9781339798158Subjects--Topical Terms:

523952
Organic chemistry.

Synthesis of fluorinated compounds by one-pot reactions and asymmetric organocatalysis.
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500 $a Adviser: Wei Zhang.
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520 $a The synthesis of organofluorine molecules has become increasingly important in medicinal and agricultural chemistry because fluorinated molecules usually have unique chemical and biological properties. Fluorination can be combined with other chemicals in one-pot synthesis to save reaction time and energy, and to reduce the amount of waste by eliminating the intermediate purification step. The first project discussed in this thesis is the fluorination of beta--keto carbonyl with Selectfluor(TM) followed by the Mannich reaction with anilines and benzaldehydes for the synthesis of alpha--fluoro and aminomethylated 1,3-dicarbonyl compounds.
520 $a Step-economic one-pot reactions, transition metal-free organocatalysis and catalyst recovery are green synthetic techniques. In the second project, one-pot Michael/aza-Henry/lactamization reaction promoted by a recyclable fluorous bifunctional cinchona alkaloid/thiourea organocatalyst was developed for asymmetric synthesis of fluorine-containing 2-piperidinones bearing four stereocenters in good yield and excellent stereoselectivity with up to 99% ee and 15:1 dr.
520 $a In the third project, a new one-pot quadruple cascade fluorination/Michael/Michael/aldol sequence for asymmetric synthesis of fluorine-containing polysubstituted cyclohexanes bearing six contiguous stereocenters was developed using the recyclable fluorous organocatalyst. The one-pot reactions gave polysubstituted cyclohexanes in 45-80% yields with up to 99% ee and 20:1 dr. The fluorous-organocatalyst was recovered from the reaction mixture in 94% yield and 98% purity by fluorous solid-phase extraction (F-SPE).
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