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Design and development of new transi...

Deschamps, Nicole Marie.

Design and development of new transition metal-catalyzed two- and three-component cycloaddition reactions.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Design and development of new transition metal-catalyzed two- and three-component cycloaddition reactions.
Author:	Deschamps, Nicole Marie.
Description:	513 p.
Notes:	Adviser: Paul A. Wender.
Notes:	Source: Dissertation Abstracts International, Volume: 67-05, Section: B, page: 2554.
Contained By:	Dissertation Abstracts International67-05B.
Subject:	Chemistry, Organic.
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3219257
ISBN:	9780542706585

Design and development of new transition metal-catalyzed two- and three-component cycloaddition reactions.
Deschamps, Nicole Marie.

Design and development of new transition metal-catalyzed two- and three-component cycloaddition reactions. - 513 p.

Adviser: Paul A. Wender.

Thesis (Ph.D.)--Stanford University, 2006.

Studies aimed at the design and development of new transition-metal catalyzed reactions involving carbon-carbon sigma bond activation have produced a new [6+1] carbonylative cycloaddition reaction. Allenylcyclobutanes undergo a strain-driven metal-catalyzed carbon-carbon bond activation reaction to generate organometallic intermediates that can be trapped with CO to produce a variety of functionalized cycloheptenones in good to excellent yields. In related investigations, a transition metal-catalyzed carbon-oxygen sigma bond activation reaction of allenyl ethers was uncovered. Allenyl ethers are converted to 2-carboalkoxy-1,3-dienes in the presence of CO in good to excellent yields under remarkably mild conditions.

ISBN: 9780542706585Subjects--Topical Terms:

193634
Chemistry, Organic.

Design and development of new transition metal-catalyzed two- and three-component cycloaddition reactions.
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100 0 $a Deschamps, Nicole Marie. $3 264140
245 1 0 $a Design and development of new transition metal-catalyzed two- and three-component cycloaddition reactions.
300 $a 513 p.
500 $a Adviser: Paul A. Wender.
500 $a Source: Dissertation Abstracts International, Volume: 67-05, Section: B, page: 2554.
502 $a Thesis (Ph.D.)--Stanford University, 2006.
520 # $a Studies aimed at the design and development of new transition-metal catalyzed reactions involving carbon-carbon sigma bond activation have produced a new [6+1] carbonylative cycloaddition reaction. Allenylcyclobutanes undergo a strain-driven metal-catalyzed carbon-carbon bond activation reaction to generate organometallic intermediates that can be trapped with CO to produce a variety of functionalized cycloheptenones in good to excellent yields. In related investigations, a transition metal-catalyzed carbon-oxygen sigma bond activation reaction of allenyl ethers was uncovered. Allenyl ethers are converted to 2-carboalkoxy-1,3-dienes in the presence of CO in good to excellent yields under remarkably mild conditions.
520 # $a The [2+2+1] reaction of diene-ynes and CO (the dienyl Pauson-Khand reaction) was designed based on the trapping of intermediates in the transition metal-catalyzed [4+2] cycloaddition reaction of diene-ynes with CO. These studies also led to the first example of a [4+2+1] reaction of diene-ynes and CO. The dienyl Pauson-Khand reaction provides an efficient and diastereoselective route to functionalized alkenylcyclopentenones. Important control studies comparing the reactivity of diene-ynes and ene-ynes in [2+2+1] cycloaddition reactions indicate that the diene accelerates the reaction. Significantly, this observation led to the design and development of three new [2+2+1] reactions based on the use of dienes as reactive two-carbon components: the intermolecular dienyl Pauson-Khand reaction, the [2+2+1] reaction of dienes, alkenes and CO, and the [2+2+1] reaction of dienes, allenes and CO. These reactions provide access to a wide variety of alkenylcyclopentanone derivatives in good to excellent yields from commercially or readily available starting materials.
520 # $a The design and development of new reactions and new strategies that predictably and efficiently provide access to structurally complex molecules from simple and readily available starting materials is a preeminent goal in organic synthesis and is critical to the advancement of the field of organic chemistry and related disciplines. A powerful approach towards achieving this goal is the design and development of transition metal-catalyzed cycloaddition reactions.
590 $a School code: 0212.
650 # 0 $a Chemistry, Organic. $3 193634
690 $a 0490
710 0 # $a Stanford University. $3 212607
773 0 # $g 67-05B. $t Dissertation Abstracts International
790 $a 0212
790 1 0 $a Wender, Paul A., $e advisor
791 $a Ph.D.
792 $a 2006
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