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I. Green Chemistry and Metathesis II...

Voigtritter, Karl Robert.

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I. Green Chemistry and Metathesis II. Copper Hydride 1,2- and 1,4-Reductions of Enones.

Record Type:	Language materials, printed : Monograph/item
Title/Author:	I. Green Chemistry and Metathesis II. Copper Hydride 1,2- and 1,4-Reductions of Enones./
Author:	Voigtritter, Karl Robert.
Description:	361 p.
Notes:	Source: Dissertation Abstracts International, Volume: 75-06(E), Section: B.
Contained By:	Dissertation Abstracts International75-06B(E).
Subject:	Chemistry, General. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3612046
ISBN:	9781303732034

I. Green Chemistry and Metathesis II. Copper Hydride 1,2- and 1,4-Reductions of Enones.
Voigtritter, Karl Robert.

I. Green Chemistry and Metathesis II. Copper Hydride 1,2- and 1,4-Reductions of Enones. - 361 p.

Source: Dissertation Abstracts International, Volume: 75-06(E), Section: B.

Thesis (Ph.D.)--University of California, Santa Barbara, 2013.

As the chemical industry is becoming more conscious about the amount of hazardous waste they are generating, green chemistry and its underlying principles are becoming more relevant. One approach that can be taken to eliminate unnecessary waste would be to remove organic solvents from organic reactions. A second approach would be to use catalysis whenever possible. Research into both of these approaches is the focus of this thesis. Nonionic surfactants in water, namely the vitamin E based amphiphiles (PTS and the newly developed TPGS-750-M), have played important roles in enabling these two approaches. Numerous transition metal catalyzed transformations can now be accomplished in water at room temperature. The Lipshutz group's chemistry in water is an important advance in surfactant technology evidenced by its recent award of the EPA's Presidential Green Chemistry Challenge Award. This thesis will detail both cross- and ring-closing metathesis, Miyaura borylations, copper hydride-catalyzed asymmetric conjugate reductions, and copper(I)/TEMPO catalyzed oxidations. The copper hydride-catalyzed conjugate reduction has become a valuable and reliable method for generating a stereocenter beta to what was an beta,beta-unsaturated system. The method is mild, and in general, selective. Curiously, when alpha-substituted or acyclic beta,beta-disubstituted enones are subjected to the reduction conditions created when nonracemic DTBM-SEGPHOS is employed; reduction of the ketone, rather than the enone takes place. The newly formed alcohols are generated in high enantiomeric excesses. A mechanistic investigation was pursued using computational chemistry.

ISBN: 9781303732034Subjects--Topical Terms:

1021807
Chemistry, General.

I. Green Chemistry and Metathesis II. Copper Hydride 1,2- and 1,4-Reductions of Enones.
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100 1 $a Voigtritter, Karl Robert. $3 2106434
245 1 0 $a I. Green Chemistry and Metathesis II. Copper Hydride 1,2- and 1,4-Reductions of Enones.
300 $a 361 p.
500 $a Source: Dissertation Abstracts International, Volume: 75-06(E), Section: B.
500 $a Advisers: Bruce H. Lipshutz; Donald H. Aue.
502 $a Thesis (Ph.D.)--University of California, Santa Barbara, 2013.
520 $a As the chemical industry is becoming more conscious about the amount of hazardous waste they are generating, green chemistry and its underlying principles are becoming more relevant. One approach that can be taken to eliminate unnecessary waste would be to remove organic solvents from organic reactions. A second approach would be to use catalysis whenever possible. Research into both of these approaches is the focus of this thesis. Nonionic surfactants in water, namely the vitamin E based amphiphiles (PTS and the newly developed TPGS-750-M), have played important roles in enabling these two approaches. Numerous transition metal catalyzed transformations can now be accomplished in water at room temperature. The Lipshutz group's chemistry in water is an important advance in surfactant technology evidenced by its recent award of the EPA's Presidential Green Chemistry Challenge Award. This thesis will detail both cross- and ring-closing metathesis, Miyaura borylations, copper hydride-catalyzed asymmetric conjugate reductions, and copper(I)/TEMPO catalyzed oxidations. The copper hydride-catalyzed conjugate reduction has become a valuable and reliable method for generating a stereocenter beta to what was an beta,beta-unsaturated system. The method is mild, and in general, selective. Curiously, when alpha-substituted or acyclic beta,beta-disubstituted enones are subjected to the reduction conditions created when nonracemic DTBM-SEGPHOS is employed; reduction of the ketone, rather than the enone takes place. The newly formed alcohols are generated in high enantiomeric excesses. A mechanistic investigation was pursued using computational chemistry.
590 $a School code: 0035.
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650 4 $a Chemistry, Inorganic. $3 517253
650 4 $a Chemistry, Organic. $3 516206
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710 2 $a University of California, Santa Barbara. $b Chemistry. $3 1029809
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