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Beyond Asymmetric Allylic Amination : = Exploring the Chemistry of Rhodium-catalyzed Reactions of Allylic Trichloroacetimidates in the Synthesis of Nitrogen and 1,2-diamine Heterocyclic Compounds.

Record Type:	Language materials, manuscript : Monograph/item
Title/Author:	Beyond Asymmetric Allylic Amination :/
Reminder of title:	Exploring the Chemistry of Rhodium-catalyzed Reactions of Allylic Trichloroacetimidates in the Synthesis of Nitrogen and 1,2-diamine Heterocyclic Compounds.
Author:	Mwenda, Edward.
Description:	1 online resource (362 pages)
Notes:	Source: Dissertation Abstracts International, Volume: 79-12(E), Section: B.
Contained By:	Dissertation Abstracts International79-12B(E).
Subject:	Organic chemistry. -
Online resource:	click for full text (PQDT)
ISBN:	9780438151543

Beyond Asymmetric Allylic Amination : = Exploring the Chemistry of Rhodium-catalyzed Reactions of Allylic Trichloroacetimidates in the Synthesis of Nitrogen and 1,2-diamine Heterocyclic Compounds.
Mwenda, Edward.

Beyond Asymmetric Allylic Amination :Exploring the Chemistry of Rhodium-catalyzed Reactions of Allylic Trichloroacetimidates in the Synthesis of Nitrogen and 1,2-diamine Heterocyclic Compounds. - 1 online resource (362 pages)

Source: Dissertation Abstracts International, Volume: 79-12(E), Section: B.

Thesis (Ph.D.)--The University of Iowa, 2018.

Includes bibliographical references

Chiral amines are ubiquitous functionalities found in the architecture of the natural world and have been embedded into materials, catalysts, pharmaceuticals, agrochemicals, and bioactive natural products. However, limited approaches are accessible for the construction of an enantioenriched tertiary or quaternary-containing amine. This thesis describes the development of new methodologies for the synthesis of 7-membered nitrogen-containing heterocycle and 1,2-diamine compounds.

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

Mode of access: World Wide Web

ISBN: 9780438151543Subjects--Topical Terms:

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

554714
Electronic books.

Beyond Asymmetric Allylic Amination : = Exploring the Chemistry of Rhodium-catalyzed Reactions of Allylic Trichloroacetimidates in the Synthesis of Nitrogen and 1,2-diamine Heterocyclic Compounds.
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245 1 0 $a Beyond Asymmetric Allylic Amination : $b Exploring the Chemistry of Rhodium-catalyzed Reactions of Allylic Trichloroacetimidates in the Synthesis of Nitrogen and 1,2-diamine Heterocyclic Compounds.
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500 $a Source: Dissertation Abstracts International, Volume: 79-12(E), Section: B.
500 $a Adviser: Hien M. Nguyen.
502 $a Thesis (Ph.D.)--The University of Iowa, 2018.
504 $a Includes bibliographical references
520 $a Chiral amines are ubiquitous functionalities found in the architecture of the natural world and have been embedded into materials, catalysts, pharmaceuticals, agrochemicals, and bioactive natural products. However, limited approaches are accessible for the construction of an enantioenriched tertiary or quaternary-containing amine. This thesis describes the development of new methodologies for the synthesis of 7-membered nitrogen-containing heterocycle and 1,2-diamine compounds.
520 $a Chapter one describes the application of dynamic kinetic asymmetric amination (DYKAT) of branched allylic acetimidates in the synthesis of 2-alkyldihydrobenzoazepin-5-ones. These 7-membered-ring aza-ketones are generated in good yield with high enantiomeric excess through sequential rhodium-catalyzed allylic amination with 2-amino aryl aldehydes followed by intramolecular olefin hydroacylation of the resulting alkenals. This two-step procedure is efficient, straightforward and convenient for the enantioselective preparation of these ring systems.
520 $a In Chapter two, we further extended the methodology towards the allylic amination of racemic secondary and tertiary allylic trichloroacetimidates possessing beta-nitrogen substituents, and proximal nitrogen-containing heterocycles, using the DYKAT transformation to provide branched allylic 1,2-diamines with high enantioselectivity. The catalytic system is versatile in the synthesis of 1,2-diamines possessing two contiguous stereocenters, with excellent diastereoselectivity. Additionally, the nitrogen-containing heterocycles suppress competing vinyl azirdine formation, allowing for the high enantioselective syntheses of 1,2-diamines possessing tertiary and quaternary centers. Chapter three gives a very brief outlook on our efforts in rhodium-catalyzed amination strategy in providing access to a variety of enantiopure alpha-fluoromethylated allylic amines.
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
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710 2 $a The University of Iowa. $b Chemistry. $3 1192002
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