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Design and synthesis of chiral ligan...

Xiao, Dengming.

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Design and synthesis of chiral ligands and their applications in asymmetric catalysis.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	Design and synthesis of chiral ligands and their applications in asymmetric catalysis./
Author:	Xiao, Dengming.
Description:	124 p.
Notes:	Adviser: Xumu Zhang.
Contained By:	Dissertation Abstracts International61-08B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9982430
ISBN:	9780599887107

Design and synthesis of chiral ligands and their applications in asymmetric catalysis.
Xiao, Dengming.

Design and synthesis of chiral ligands and their applications in asymmetric catalysis. - 124 p.

Adviser: Xumu Zhang.

Thesis (Ph.D.)--The Pennsylvania State University, 2000.

Two families of chiral ligands were designed and synthesized. One was made from para-substituted benzene and the other one was synthesized from chiral Binol through a key intermediate 1,1'-dichloromethyl binaphthyl. These novel chiral ligands allowed us to explore a lot of useful applications in asymmetric catalysis.

ISBN: 9780599887107Subjects--Topical Terms:

516206
Chemistry, Organic.

Design and synthesis of chiral ligands and their applications in asymmetric catalysis.
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005 20110524
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020 $a 9780599887107
035 $a (UMI)AAI9982430
035 $a AAI9982430
040 $a UMI $c UMI
100 1 $a Xiao, Dengming. $3 1271819
245 1 0 $a Design and synthesis of chiral ligands and their applications in asymmetric catalysis.
300 $a 124 p.
500 $a Adviser: Xumu Zhang.
500 $a Source: Dissertation Abstracts International, Volume: 61-08, Section: B, page: 4166.
502 $a Thesis (Ph.D.)--The Pennsylvania State University, 2000.
520 $a Two families of chiral ligands were designed and synthesized. One was made from para-substituted benzene and the other one was synthesized from chiral Binol through a key intermediate 1,1'-dichloromethyl binaphthyl. These novel chiral ligands allowed us to explore a lot of useful applications in asymmetric catalysis.
520 $a Monophosphine PBH with a bicyclic [2,2,1] structure was found excellent performance in Pd-catalyzed allylic alkylation reaction (>99% ee) and phosphine catalyzed [3+2] cycloaddition reaction (93% ee). A mechanistic rationale was provided in [3+2] cycloaddition reaction.
520 $a Asymmetric hydrogenations of different substrates have been extensively studied with the transition metal-phosphine complex as the catalysts. Cationic Rh-PennPhos was proved highly effective in enantioselective hydrogenation of cyclic enol acetates and enamides (up to 99% ee) while other chiral ligands such as BINAP and DuPhos gave very low enantioselectivities. The highest enantioselectivity (up to 99% ee) was achieved in asymmetric hydrogenation of electron rich trisubstituted enamides (for mixture of isomer ( E) and (Z)) with Rh-Binaphane as catalyst. The Ir-f-Binaphane complex showed high enantioselectivity (96% ee) on hydrogenation of (E)-beta-dehydroaminoacid and lower enantioselectivity on (Z)-beta-dehydroaminoacid.
520 $a The simple ketone, one of the toughest substrates in asymmetric hydrogenation, was reduced by Rh-PennPhos complex with high enantioselectivity (up to 95% ee). Unprecedented results (75--94% ee) were obtained in Rh- PennPhos catalyzed hydrogenation of alkyl-alkyl ketones. A pull-push mechanism for asymmetric hydrogenation of simple ketones was proposed based on the interesting additive effect in the reaction.
520 $a Highly Enantioselective hydrogenation of N-arylimines was accomplished by employing the Ir-f-Binaphane complex as the catalyst. The highest enantiselectivity (up to 99% ee) was achieved on the hydrogenation of N-(1-phenylethylidene)2,6-xylxlamine. The aryl groups in the substrate play a very important role in highly asymmetric induction. Additive I2 was proved very effective in increasing the enantioselectivity and reactivity for hydrogenation of some substrates while ineffective for other substrates. Different mechanism was proposed to explain the observations. A new synthetic route to make primary chiral amines was developed based on new methodology. Potential application of Ir- f-Binaphane in asymmetric hydrogenation of MEA-imine to synthesize chiral agrochemical (S)-Metolachlor was envisioned.
590 $a School code: 0176.
650 4 $a Chemistry, Organic. $3 516206
690 $a 0490
710 2 0 $a The Pennsylvania State University. $3 699896
773 0 $t Dissertation Abstracts International $g 61-08B.
790 $a 0176
790 1 0 $a Zhang, Xumu, $e advisor
791 $a Ph.D.
792 $a 2000
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=9982430