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Asymmetric Synthesis of Amines via M...

Buesking, Andrew.

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Asymmetric Synthesis of Amines via Metal-Catalyzed Additions of Organometallic Reagents.

紀錄類型:	書目-電子資源 : Monograph/item
正題名/作者:	Asymmetric Synthesis of Amines via Metal-Catalyzed Additions of Organometallic Reagents./
作者:	Buesking, Andrew.
面頁冊數:	299 p.
附註:	Source: Dissertation Abstracts International, Volume: 75-09(E), Section: B.
Contained By:	Dissertation Abstracts International75-09B(E).
標題:	Chemistry. -
電子資源:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3580644
ISBN:	9781321050660

Asymmetric Synthesis of Amines via Metal-Catalyzed Additions of Organometallic Reagents.
Buesking, Andrew.

Asymmetric Synthesis of Amines via Metal-Catalyzed Additions of Organometallic Reagents. - 299 p.

Source: Dissertation Abstracts International, Volume: 75-09(E), Section: B.

Thesis (Ph.D.)--Yale University, 2014.

With greater than 80% of all drugs and drug candidates containing the amine functionality,1 the amine is one of the most prevalent functional groups in medicinal chemistry. As a result, new methods to access amine products are critically important. Additions of nucleophiles to N tert-butanesulfinyl imines are one of the most prevalent approaches for the asymmetric synthesis of amines. Extensive reviews of N-tert -butanesulfinamide chemistry have been published recently, 2 and this thesis will not try to replicate those works. Instead, new methods to synthesize amines via sulfinamide chemistry and the literature relevant to these methods will be discussed.

ISBN: 9781321050660Subjects--Topical Terms:

516420
Chemistry.

Asymmetric Synthesis of Amines via Metal-Catalyzed Additions of Organometallic Reagents.
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245 1 0 $a Asymmetric Synthesis of Amines via Metal-Catalyzed Additions of Organometallic Reagents.
300 $a 299 p.
500 $a Source: Dissertation Abstracts International, Volume: 75-09(E), Section: B.
500 $a Adviser: Jonathan Ellman.
502 $a Thesis (Ph.D.)--Yale University, 2014.
520 $a With greater than 80% of all drugs and drug candidates containing the amine functionality,1 the amine is one of the most prevalent functional groups in medicinal chemistry. As a result, new methods to access amine products are critically important. Additions of nucleophiles to N tert-butanesulfinyl imines are one of the most prevalent approaches for the asymmetric synthesis of amines. Extensive reviews of N-tert -butanesulfinamide chemistry have been published recently, 2 and this thesis will not try to replicate those works. Instead, new methods to synthesize amines via sulfinamide chemistry and the literature relevant to these methods will be discussed.
520 $a Chapter 1 describes the first examples of Rh-catalyzed additions of aryl boron reagents to N-suflinyl ketimines, which access six important classes of tertiary carbinamine pharniacophores. Additions to highly activated N-tert-butanesulfinyl ketimines derived from 3-oxetanone, 3-azetidinone, and isatin proceed in excellent yields and in the case of isatin-derived ketimines with excellent diastereoselectivity. Additionally, less activated N-sulfinyl ketimines derived from cyclohexanone, piperidin-4-one, and tetrahydropyran-4-one react readily under similar conditions when employing the less hindered isopropanesulfinyl group. An improved synthesis of isopropanesulfinamide and recycling of the isopropylsulfinyl group are also reported.
520 $a Chapter 2 details the development of additions of Knochel-type benzyl zinc reagents to N-tert-butanesuflinyl aldimines. Notably, additions of these sp3-hybridized reagents demonstrate good functional-group compatibility, adding chemoselectively to imines in the presence of esters and nitriles. Moreover, addition to a glyceraldehyde-derived N-tert- butanesulfinyl imine proceeds in high yield and with exceptional selectivity to provide rapid entry to hydroxyethylamine-based aspartyl protease inhibitors.
520 $a Chapter 3 describes additions of alpha-amido trifluoroborates to carbonyl derivatives, which represent the first application of alpha-amino boronic acid derivatives in Rh-catalyzed couplings. Reactions of alpha-sulf namido trifluoroborates with trifluoromethyl ketones proceed in reasonable yields and with good diastereoselectivity. The potential of this method is further highlighted by the exploration of a variety of nitrogen substituents and addition to other electrophiles including benzaldehyde and trityl-protected isatin.
520 $a Chapter 4 details the development of an improved method to access synthetically useful and pharmaceutically relevant alpha-amino boronic acid derivatives. The asymmetric borylation of N-tert-butanesulfinyl imines with bis(pinacolato)diboron is achieved using a Cu(II) catalyst system. The Cu(II)-catalyzed reaction is performed on the benchtop in air at room temperature using commercially available and inexpensive reagents at low catalyst loadings. A variety of N-tert-butanesulfinyl imines, including ketimines, react readily to provide the corresponding a-sulfinamido boronate esters in good yields and with high stereoselectivity. This transformation is also applied to the telescoped synthesis of a-sulfinamido trifluoroborates.
590 $a School code: 0265.
650 4 $a Chemistry. $3 516420
650 4 $a Organic chemistry. $3 523952
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710 2 $a Yale University. $3 515640
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793 $a English
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