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Expanding the Electrophile and Nucle...

Scaggs, W. Rush.

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Expanding the Electrophile and Nucleophile Scope in Palladium/Lewis Base Cooperative Catalysis.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Expanding the Electrophile and Nucleophile Scope in Palladium/Lewis Base Cooperative Catalysis./
Author:	Scaggs, W. Rush.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2019,
Description:	425 p.
Notes:	Source: Dissertations Abstracts International, Volume: 81-08, Section: B.
Contained By:	Dissertations Abstracts International81-08B.
Subject:	Organic chemistry. -
Online resource:	https://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=27670291
ISBN:	9781392823781

Expanding the Electrophile and Nucleophile Scope in Palladium/Lewis Base Cooperative Catalysis.
Scaggs, W. Rush.

Expanding the Electrophile and Nucleophile Scope in Palladium/Lewis Base Cooperative Catalysis. - Ann Arbor : ProQuest Dissertations & Theses, 2019 - 425 p.

Source: Dissertations Abstracts International, Volume: 81-08, Section: B.

Thesis (Ph.D.)--Indiana University, 2019.

This item must not be sold to any third party vendors.

The enantioselective allylic alkylation of acyclic prochiral nucleophiles with π(allyl) palladium electrophiles to form a-asymmetric tertiary centers has challenged chemists for years. Difficulties associated with this transformation include: 1) control over enolate geometry of the prochiral nucleophile, 2) the propensity of enantioenriched tertiary centers to racemize in the presence of strong bases, and 3) no obvious way to control enantioselectivity of the transformation apart from chiral ligands on palladium. To address the challenges of reactivity and enantioselectivity, we turned to C1-ammonium enolates generated via Lewis base catalysis with chiral tertiary amines. Removing enantiocontrol from the electrophile has allowed us to expand the range, and explore the reactivity, of π(allyl)Pd species that are limited in the literature and permitted the synthesis of functionalized products in high enantiomeric ratios. This document describes the expansion of the electrophile and nucleophile scopes in our cooperative catalysis.

ISBN: 9781392823781Subjects--Topical Terms:

523952
Organic chemistry.
Subjects--Index Terms:

Cooperative Catalysis

Expanding the Electrophile and Nucleophile Scope in Palladium/Lewis Base Cooperative Catalysis.
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245 1 0 $a Expanding the Electrophile and Nucleophile Scope in Palladium/Lewis Base Cooperative Catalysis.
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300 $a 425 p.
500 $a Source: Dissertations Abstracts International, Volume: 81-08, Section: B.
500 $a Advisor: Snaddon, Thomas N.
502 $a Thesis (Ph.D.)--Indiana University, 2019.
506 $a This item must not be sold to any third party vendors.
520 $a The enantioselective allylic alkylation of acyclic prochiral nucleophiles with π(allyl) palladium electrophiles to form a-asymmetric tertiary centers has challenged chemists for years. Difficulties associated with this transformation include: 1) control over enolate geometry of the prochiral nucleophile, 2) the propensity of enantioenriched tertiary centers to racemize in the presence of strong bases, and 3) no obvious way to control enantioselectivity of the transformation apart from chiral ligands on palladium. To address the challenges of reactivity and enantioselectivity, we turned to C1-ammonium enolates generated via Lewis base catalysis with chiral tertiary amines. Removing enantiocontrol from the electrophile has allowed us to expand the range, and explore the reactivity, of π(allyl)Pd species that are limited in the literature and permitted the synthesis of functionalized products in high enantiomeric ratios. This document describes the expansion of the electrophile and nucleophile scopes in our cooperative catalysis.
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653 $a Lewis Base
653 $a Palladium
653 $a Pi-allyl
653 $a Transition metal
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