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Palladium catalyzed asymmetric allyl...
~
Jiang, Chunhui.
Palladium catalyzed asymmetric allylic alkylation and TMM cycloaddition in natural product syntheses.
紀錄類型:
書目-電子資源 : Monograph/item
正題名/作者:
Palladium catalyzed asymmetric allylic alkylation and TMM cycloaddition in natural product syntheses.
作者:
Jiang, Chunhui.
面頁冊數:
394 p.
附註:
Adviser: Barry M. Trost.
附註:
Source: Dissertation Abstracts International, Volume: 65-11, Section: B, page: 5728.
Contained By:
Dissertation Abstracts International65-11B.
標題:
Chemistry, Organic.
電子資源:
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.
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Palladium catalyzed asymmetric allylic alkylation and TMM cycloaddition in natural product syntheses.
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Thesis (Ph.D.)--Stanford University, 2005.
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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.
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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.
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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.
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