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Enantioselective Synthesis and Stere...

Edelstein, Emma Kate.

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Enantioselective Synthesis and Stereospecific Transformations of Organoboronic Esters.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Enantioselective Synthesis and Stereospecific Transformations of Organoboronic Esters./
Author:	Edelstein, Emma Kate.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2018,
Description:	972 p.
Notes:	Source: Dissertations Abstracts International, Volume: 79-12, Section: B.
Contained By:	Dissertations Abstracts International79-12B.
Subject:	Chemistry. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=10816998
ISBN:	9780355971460

Enantioselective Synthesis and Stereospecific Transformations of Organoboronic Esters.
Edelstein, Emma Kate.

Enantioselective Synthesis and Stereospecific Transformations of Organoboronic Esters. - Ann Arbor : ProQuest Dissertations & Theses, 2018 - 972 p.

Source: Dissertations Abstracts International, Volume: 79-12, Section: B.

Thesis (Ph.D.)--Boston College, 2018.

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

This dissertation details the development of several enantioselective or stereospecific transformations involving organoboronic esters. Chapter one will introduce electrophile-induced boronate rearrangements which underpins much of the reactivity that will be discussed in subsequent chapters. In chapter two the conjunctive cross-coupling reaction is presented. Its development and application to the synthesis of non-racemic boronic esters, along with its application to the synthesis of enantioenriched allylic boronic esters, will be discussed. In chapter three the cross-coupling of geminal bis(boronic) esters is introduced and the development of a method to employ them in cross-coupling with alkenyl bromides, affording enantioenriched substituted allylic boronic esters is outlined. In chapter four we highlight the utility of allylic boronic esters, and detail the development of a cross-coupling reaction that involves the use of these substrates and halide electrophiles to furnish enantiomerically enriched products containing all carbon quaternary stereocenters. Finally, in chapter five we describe the development of a metalfree amination reaction of organoboron compounds, which is able to deliver otherwise difficult-to-access enantiomerically enriched α-tertiary amines.

ISBN: 9780355971460Subjects--Topical Terms:

516420
Chemistry.

Enantioselective Synthesis and Stereospecific Transformations of Organoboronic Esters.
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100 1 $a Edelstein, Emma Kate. $3 3434557
245 1 0 $a Enantioselective Synthesis and Stereospecific Transformations of Organoboronic Esters.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2018
300 $a 972 p.
500 $a Source: Dissertations Abstracts International, Volume: 79-12, Section: B.
500 $a Publisher info.: Dissertation/Thesis.
500 $a Advisor: Morken, James P.
502 $a Thesis (Ph.D.)--Boston College, 2018.
506 $a This item must not be sold to any third party vendors.
520 $a This dissertation details the development of several enantioselective or stereospecific transformations involving organoboronic esters. Chapter one will introduce electrophile-induced boronate rearrangements which underpins much of the reactivity that will be discussed in subsequent chapters. In chapter two the conjunctive cross-coupling reaction is presented. Its development and application to the synthesis of non-racemic boronic esters, along with its application to the synthesis of enantioenriched allylic boronic esters, will be discussed. In chapter three the cross-coupling of geminal bis(boronic) esters is introduced and the development of a method to employ them in cross-coupling with alkenyl bromides, affording enantioenriched substituted allylic boronic esters is outlined. In chapter four we highlight the utility of allylic boronic esters, and detail the development of a cross-coupling reaction that involves the use of these substrates and halide electrophiles to furnish enantiomerically enriched products containing all carbon quaternary stereocenters. Finally, in chapter five we describe the development of a metalfree amination reaction of organoboron compounds, which is able to deliver otherwise difficult-to-access enantiomerically enriched α-tertiary amines.
590 $a School code: 0016.
650 4 $a Chemistry. $3 516420
650 4 $a Organic chemistry. $3 523952
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710 2 $a Boston College. $b GSAS - Chemistry. $3 2094863
773 0 $t Dissertations Abstracts International $g 79-12B.
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