國立高雄大學圖資館 |

Language: English

Back

Palladium catalyzed asymmetric allyl...

Jiang, Chunhui.

Palladium catalyzed asymmetric allylic alkylation and TMM cycloaddition in natural product syntheses.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Palladium catalyzed asymmetric allylic alkylation and TMM cycloaddition in natural product syntheses.
Author:	Jiang, Chunhui.
Description:	394 p.
Notes:	Adviser: Barry M. Trost.
Notes:	Source: Dissertation Abstracts International, Volume: 65-11, Section: B, page: 5728.
Contained By:	Dissertation Abstracts International65-11B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3153116
ISBN:	0496135619

Palladium catalyzed asymmetric allylic alkylation and TMM cycloaddition in natural product syntheses.
Jiang, Chunhui.

Palladium catalyzed asymmetric allylic alkylation and TMM cycloaddition in natural product syntheses. - 394 p.

Adviser: Barry M. Trost.

Thesis (Ph.D.)--Stanford University, 2005.

Palladium catalyzed regio- and enantioselective ring openings of vinyl epoxides with carbon and nitrogen centered nucleophiles are developed and optimized. Chiral ligands can control regio- as well as enantioselectivities in the reactions of isoprene monoepoxide. Thus 1,2- rather than 1,4-adducts with carbon nucleophiles such as beta-ketoesters and nitrogen nucleophiles such as PMBNH2 are obtained with excellent enantioselectivities and good yields. The results with beta-ketoesters represent the first examples of such reactions for carbon centered nucleophiles reacting with vinyl epoxides, which are even more remarkable since a quaternary stereocenter is constructed enantioselectively.

ISBN: 0496135619Subjects--Topical Terms:

193634
Chemistry, Organic.

Palladium catalyzed asymmetric allylic alkylation and TMM cycloaddition in natural product syntheses.
LDR:02520nmm _2200277 _450 001 167287
005 20061005085840.5
008 090528s2005 eng d
020 $a 0496135619
035 $a 00197903
040 $a UnM $c UnM
100 0 $a Jiang, Chunhui. $3 237433
245 1 0 $a Palladium catalyzed asymmetric allylic alkylation and TMM cycloaddition in natural product syntheses.
300 $a 394 p.
500 $a Adviser: Barry M. Trost.
500 $a Source: Dissertation Abstracts International, Volume: 65-11, Section: B, page: 5728.
502 $a Thesis (Ph.D.)--Stanford University, 2005.
520 # $a Palladium catalyzed regio- and enantioselective ring openings of vinyl epoxides with carbon and nitrogen centered nucleophiles are developed and optimized. Chiral ligands can control regio- as well as enantioselectivities in the reactions of isoprene monoepoxide. Thus 1,2- rather than 1,4-adducts with carbon nucleophiles such as beta-ketoesters and nitrogen nucleophiles such as PMBNH2 are obtained with excellent enantioselectivities and good yields. The results with beta-ketoesters represent the first examples of such reactions for carbon centered nucleophiles reacting with vinyl epoxides, which are even more remarkable since a quaternary stereocenter is constructed enantioselectively.
520 # $a The synthetic power of the above methodologies is subsequently demonstrated in the asymmetric syntheses of the cyclopentyl core of viridenomycin and a derivative of vancosamine. The cyclopentyl core of viridenomycin was synthesized in 11 steps and 20.2% overall yield, which contrasts sharply with the two existing routes, the shorter of which required nearly twice as many steps. The derivative of vancosamine is synthesized in 9 total steps and 28.6% overall yield, which is the first asymmetric synthesis of vancosamine derivatives using a non-enzyme-catalyzed enantioselective reaction as the source of chirality.
520 # $a The total synthesis of marcfortine A and B are also investigated, in which a Pd-catalyzed carboxylative TMM cycloaddition is a key step. The studies are focused on the cyclization of the bicyclo[2.2.2]diazaoctane system.
590 $a School code: 0212.
650 # 0 $a Chemistry, Organic. $3 193634
690 $a 0490
710 0 # $a Stanford University. $3 212607
773 0 # $g 65-11B. $t Dissertation Abstracts International
790 $a 0212
790 1 0 $a Trost, Barry M., $e advisor
791 $a Ph.D.
792 $a 2005
856 4 0 $u http://libsw.nuk.edu.tw:81/login?url=http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3153116 $z http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3153116