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Asymmetric, catalytic aziridination ...

Li, Zhen.

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Asymmetric, catalytic aziridination and aziridine ring-opening reactions.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Asymmetric, catalytic aziridination and aziridine ring-opening reactions./
Author:	Li, Zhen.
Description:	176 p.
Notes:	Adviser: Eric N. Jacobsen.
Contained By:	Dissertation Abstracts International58-05B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9733348
ISBN:	059142861X

Asymmetric, catalytic aziridination and aziridine ring-opening reactions.
Li, Zhen.

Asymmetric, catalytic aziridination and aziridine ring-opening reactions. - 176 p.

Adviser: Eric N. Jacobsen.

Thesis (Ph.D.)--Harvard University, 1997.

The first chapter of the thesis documents the discovery of a new class of chiral diimine ligands for asymmetric catalytic aziridination of alkenes. These ligands are remarkably simple, yet potentially versatile templates for asymmetric catalysis. They are less rigid than either the bis-oxazoline or salen ligands, yet are clearly capable of highly effective stereochemical communication in a metal-mediated process. Their synthetic accessibility renders them amenable to the systematic variation of both steric and electronic properties. A variety of olefins were aziridinated with moderate to excellent enantioselectivities and yields using the (diimine)copper (I) system as the catalyst.

ISBN: 059142861XSubjects--Topical Terms:

516206
Chemistry, Organic.

Asymmetric, catalytic aziridination and aziridine ring-opening reactions.
LDR:02445nam 2200289 a 45 001 933454
005 20110505
008 110505s1997 eng d
020 $a 059142861X
035 $a (UnM)AAI9733348
035 $a AAI9733348
040 $a UnM $c UnM
100 1 $a Li, Zhen. $3 1257184
245 1 0 $a Asymmetric, catalytic aziridination and aziridine ring-opening reactions.
300 $a 176 p.
500 $a Adviser: Eric N. Jacobsen.
500 $a Source: Dissertation Abstracts International, Volume: 58-05, Section: B, page: 2427.
502 $a Thesis (Ph.D.)--Harvard University, 1997.
520 $a The first chapter of the thesis documents the discovery of a new class of chiral diimine ligands for asymmetric catalytic aziridination of alkenes. These ligands are remarkably simple, yet potentially versatile templates for asymmetric catalysis. They are less rigid than either the bis-oxazoline or salen ligands, yet are clearly capable of highly effective stereochemical communication in a metal-mediated process. Their synthetic accessibility renders them amenable to the systematic variation of both steric and electronic properties. A variety of olefins were aziridinated with moderate to excellent enantioselectivities and yields using the (diimine)copper (I) system as the catalyst.
520 $a The second chapter describes the investigation of the mechanism of the (diimine)copper-catalyzed aziridination reaction. Several experimental observations provide evidence that this reaction involves the intermediacy of a discrete, monomeric Cu(III)-nitrene complex.
520 $a The last chapter of the thesis describes our achievement of the first enantioselective catalytic aziridine ring-opening reaction. It was uncovered that the aminoindanol-derived tridentate ligand$\cdot $c r(III) complex is an effective catalyst for the reaction. In the presence of the catalyst, very good-to-excellent enantioselectivities and yields have been attained in the ring-opening of a range of meso-aziridines. Combined with existing effective synthetic routes to aziridines, the enantioselective ring-opening reaction provides a viable method for the synthesis of valuable chiral building blocks.
590 $a School code: 0084.
650 4 $a Chemistry, Organic. $3 516206
690 $a 0490
710 2 0 $a Harvard University. $3 528741
773 0 $t Dissertation Abstracts International $g 58-05B.
790 $a 0084
790 1 0 $a Jacobsen, Eric N., $e advisor
791 $a Ph.D.
792 $a 1997
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9733348