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Asymmetric Conjugated Addition of Ca...

Eickhoff, John Adam.

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Asymmetric Conjugated Addition of Carboxylic Acids with Traceless Chiral Lithium Amides and Synthesis of alpha-Substituted Ketones and 2-Aminoazoles from Thioesters via Copper-Mediated Cross-Coupling.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Asymmetric Conjugated Addition of Carboxylic Acids with Traceless Chiral Lithium Amides and Synthesis of alpha-Substituted Ketones and 2-Aminoazoles from Thioesters via Copper-Mediated Cross-Coupling./
Author:	Eickhoff, John Adam.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2018,
Description:	124 p.
Notes:	Source: Masters Abstracts International, Volume: 57-05.
Contained By:	Masters Abstracts International57-05(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10751654
ISBN:	9780355876673

Asymmetric Conjugated Addition of Carboxylic Acids with Traceless Chiral Lithium Amides and Synthesis of alpha-Substituted Ketones and 2-Aminoazoles from Thioesters via Copper-Mediated Cross-Coupling.
Eickhoff, John Adam.

Asymmetric Conjugated Addition of Carboxylic Acids with Traceless Chiral Lithium Amides and Synthesis of alpha-Substituted Ketones and 2-Aminoazoles from Thioesters via Copper-Mediated Cross-Coupling. - Ann Arbor : ProQuest Dissertations & Theses, 2018 - 124 p.

Source: Masters Abstracts International, Volume: 57-05.

Thesis (M.S.)--University of California, Santa Barbara, 2018.

Michael addition is a premier synthetic method for carbon--carbon and carbon--heteroatom bond formation. Using chiral dilithium amides as traceless auxiliaries, we report the direct enantioselective Michael addition of carboxylic acids. A free carboxyl group in the product provides versatility for further functionalization, and the chiral reagent can be readily recovered by extraction with aqueous acid. The method has been applied in the enantioselective total synthesis of the purported structure of pulveraven B.

ISBN: 9780355876673Subjects--Topical Terms:

523952
Organic chemistry.

Asymmetric Conjugated Addition of Carboxylic Acids with Traceless Chiral Lithium Amides and Synthesis of alpha-Substituted Ketones and 2-Aminoazoles from Thioesters via Copper-Mediated Cross-Coupling.
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100 1 $a Eickhoff, John Adam. $3 3351881
245 1 0 $a Asymmetric Conjugated Addition of Carboxylic Acids with Traceless Chiral Lithium Amides and Synthesis of alpha-Substituted Ketones and 2-Aminoazoles from Thioesters via Copper-Mediated Cross-Coupling.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2018
300 $a 124 p.
500 $a Source: Masters Abstracts International, Volume: 57-05.
500 $a Includes supplementary digital materials.
500 $a Adviser: Armen Zakarian.
502 $a Thesis (M.S.)--University of California, Santa Barbara, 2018.
520 $a Michael addition is a premier synthetic method for carbon--carbon and carbon--heteroatom bond formation. Using chiral dilithium amides as traceless auxiliaries, we report the direct enantioselective Michael addition of carboxylic acids. A free carboxyl group in the product provides versatility for further functionalization, and the chiral reagent can be readily recovered by extraction with aqueous acid. The method has been applied in the enantioselective total synthesis of the purported structure of pulveraven B.
520 $a Facile synthesis of a variety of alpha-heterosubstituted ketones under mild conditions was achieved by copper-mediated cross-coupling of thioesters with functionalized organostannanes. Application of this coupling methodology provided a concise pathway for the conversion of carboxylic acids to 2-aminoimidazoles, 2-aminothiazoles, and 2-aminooxazoles via thioesters in practical yields.
590 $a School code: 0035.
650 4 $a Organic chemistry. $3 523952
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710 2 $a University of California, Santa Barbara. $b Chemistry. $3 1029809
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791 $a M.S.
792 $a 2018
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