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Development and Applications of Novel [2+2] and [4+2] Cycloadditions.

Record Type:	Language materials, manuscript : Monograph/item
Title/Author:	Development and Applications of Novel [2+2] and [4+2] Cycloadditions./
Author:	Witherspoon, Brittany P.
Description:	1 online resource (436 pages)
Notes:	Source: Dissertation Abstracts International, Volume: 79-08(E), Section: B.
Contained By:	Dissertation Abstracts International79-08B(E).
Subject:	Organic chemistry. -
Online resource:	click for full text (PQDT)
ISBN:	9780355779653

Development and Applications of Novel [2+2] and [4+2] Cycloadditions.
Witherspoon, Brittany P.

Development and Applications of Novel [2+2] and [4+2] Cycloadditions. - 1 online resource (436 pages)

Source: Dissertation Abstracts International, Volume: 79-08(E), Section: B.

Thesis (Ph.D.)--Indiana University, 2018.

Includes bibliographical references

The enantioselective synthesis of cyclobutane derivatives has been a longstanding interest in organic chemistry. This is due to its synthetic versatility as the cyclobutane framework is susceptible to a variety of transformations towards more complex structures. Additionally, a significant amount of biologically relevant molecules contain the cyclobutane framework. Many of these molecules and their derivatives have emerged as promising candidates in drug discovery because their rigid structures have shown to be a factor in potency. Hence, chiral cyclobutanes and their derivatives have been inspiring targets to pursue in method development.

Electronic reproduction.
Ann Arbor, Mich. :
ProQuest,
2018

Mode of access: World Wide Web

ISBN: 9780355779653Subjects--Topical Terms:

1148722
Organic chemistry.
Index Terms--Genre/Form:

554714
Electronic books.

Development and Applications of Novel [2+2] and [4+2] Cycloadditions.
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245 1 0 $a Development and Applications of Novel [2+2] and [4+2] Cycloadditions.
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300 $a 1 online resource (436 pages)
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500 $a Source: Dissertation Abstracts International, Volume: 79-08(E), Section: B.
500 $a Adviser: Michael K. Brown.
502 $a Thesis (Ph.D.)--Indiana University, 2018.
504 $a Includes bibliographical references
520 $a The enantioselective synthesis of cyclobutane derivatives has been a longstanding interest in organic chemistry. This is due to its synthetic versatility as the cyclobutane framework is susceptible to a variety of transformations towards more complex structures. Additionally, a significant amount of biologically relevant molecules contain the cyclobutane framework. Many of these molecules and their derivatives have emerged as promising candidates in drug discovery because their rigid structures have shown to be a factor in potency. Hence, chiral cyclobutanes and their derivatives have been inspiring targets to pursue in method development.
520 $a In that regard, the first intramolecular chirality transfer [2+2] cycloaddition of allenic ketones and alkenes has been developed to access chiral cyclobutanes and their derivatives. This method depends upon the enantioselective synthesis of allenic ketones and efficient transfer of chirality from starting material to product. With access to a variety of products from this method, it has been applied to the enantioselective synthesis of benzocyclobutenes, which is difficult to achieve by alternative means, and it has been applied to the enantioselective total synthesis of Cajanusine, which is a complex molecule that exhibits inhibitory action against the development of hepatocellular carcinoma cells.
520 $a A novel [4+2] cycloaddition of alkenylboranes and alkenes has also been developed. This is a significant method because the enantioenriched products accessed are synthetically versatile intermediates that could be obtained in high degrees of enantioselectivity, and because the process provides an interesting mechanistic perspective of alkenylborane-alkene [4+2] cycloadditions using an oxazaborolidine backbone.
533 $a Electronic reproduction. $b Ann Arbor, Mich. : $c ProQuest, $d 2018
538 $a Mode of access: World Wide Web
650 4 $a Organic chemistry. $3 1148722
655 7 $a Electronic books. $2 local $3 554714
690 $a 0490
710 2 $a ProQuest Information and Learning Co. $3 1178819
710 2 $a Indiana University. $b Chemistry. $3 1192664
773 0 $t Dissertation Abstracts International $g 79-08B(E).
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