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Radical Cation Diels--Alder Cycloadd...

Lin, Shishi.

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Radical Cation Diels--Alder Cycloaddition Reactions By Visible Light Photocatalysis.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Radical Cation Diels--Alder Cycloaddition Reactions By Visible Light Photocatalysis./
Author:	Lin, Shishi.
Description:	261 p.
Notes:	Source: Dissertation Abstracts International, Volume: 76-06(E), Section: B.
Contained By:	Dissertation Abstracts International76-06B(E).
Subject:	Organic chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3680602
ISBN:	9781321526790

Radical Cation Diels--Alder Cycloaddition Reactions By Visible Light Photocatalysis.
Lin, Shishi.

Radical Cation Diels--Alder Cycloaddition Reactions By Visible Light Photocatalysis. - 261 p.

Source: Dissertation Abstracts International, Volume: 76-06(E), Section: B.

Thesis (Ph.D.)--The University of Wisconsin - Madison, 2015.

Electronically mismatched Diels-Alder reactions have always been a challenge to perform under mild conditions, since conventional Diels-Alder cycloadditions typically involve an electron deficient dienophile and an electron rich diene. Given the synthetic utility of electronically mismatched Diels-Alder cycloadducts, which are ubiquitously found in numerous biologically useful natural products, the research herein describes an efficient way to synthesize these cycloadducts via visible light photocatalysis. Using ruthenium polypyridyl complexes as photocatalysts, mechanistically distinct pathways for the intra- as well as intermolecular cycloaddition reactions have been developed. Our understanding of the reaction systems enabled the design of a cleavable redox auxilliary that allows efficient access to simple unfunctionalized cyclohexene adducts. The synthetic utility of the method has been illustrated in the first reported biomimetic synthesis of the natural product heitziamide A. As such, this novel methodology enables easy access towards synthetically useful cycloadducts which would otherwise be difficult or impossible.

ISBN: 9781321526790Subjects--Topical Terms:

523952
Organic chemistry.

Radical Cation Diels--Alder Cycloaddition Reactions By Visible Light Photocatalysis.
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245 1 0 $a Radical Cation Diels--Alder Cycloaddition Reactions By Visible Light Photocatalysis.
300 $a 261 p.
500 $a Source: Dissertation Abstracts International, Volume: 76-06(E), Section: B.
500 $a Adviser: Tehshik P. Yoon.
502 $a Thesis (Ph.D.)--The University of Wisconsin - Madison, 2015.
520 $a Electronically mismatched Diels-Alder reactions have always been a challenge to perform under mild conditions, since conventional Diels-Alder cycloadditions typically involve an electron deficient dienophile and an electron rich diene. Given the synthetic utility of electronically mismatched Diels-Alder cycloadducts, which are ubiquitously found in numerous biologically useful natural products, the research herein describes an efficient way to synthesize these cycloadducts via visible light photocatalysis. Using ruthenium polypyridyl complexes as photocatalysts, mechanistically distinct pathways for the intra- as well as intermolecular cycloaddition reactions have been developed. Our understanding of the reaction systems enabled the design of a cleavable redox auxilliary that allows efficient access to simple unfunctionalized cyclohexene adducts. The synthetic utility of the method has been illustrated in the first reported biomimetic synthesis of the natural product heitziamide A. As such, this novel methodology enables easy access towards synthetically useful cycloadducts which would otherwise be difficult or impossible.
590 $a School code: 0262.
650 4 $a Organic chemistry. $3 523952
650 4 $a Inorganic chemistry. $3 3173556
690 $a 0490
690 $a 0488
710 2 $a The University of Wisconsin - Madison. $b Chemistry. $3 2049906
773 0 $t Dissertation Abstracts International $g 76-06B(E).
790 $a 0262
791 $a Ph.D.
792 $a 2015
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3680602