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Rhodium-catalyzed carbocyclization r...

Indiana University., Chemistry.

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Rhodium-catalyzed carbocyclization reactions for the synthesis of five- and six-membered rings.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Rhodium-catalyzed carbocyclization reactions for the synthesis of five- and six-membered rings./
Author:	Sawyer, James R.
Description:	451 p.
Notes:	Adviser: P. Andrew Evans.
Contained By:	Dissertation Abstracts International69-08B.
Subject:	Chemistry, Inorganic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3319834
ISBN:	9780549701828

Rhodium-catalyzed carbocyclization reactions for the synthesis of five- and six-membered rings.
Sawyer, James R.

Rhodium-catalyzed carbocyclization reactions for the synthesis of five- and six-membered rings. - 451 p.

Adviser: P. Andrew Evans.

Thesis (Ph.D.)--Indiana University, 2008.

Transition metal-catalyzed carbocyclization reactions are a powerful class of transformations that provide a selective and expeditious means of synthesizing target molecules by a means that is often not accessible via traditional reactions. In particular, rhodium(I) catalysts have received a significant amount of attention due to their unique reactivity in comparison to other metals.

ISBN: 9780549701828Subjects--Topical Terms:

517253
Chemistry, Inorganic.

Rhodium-catalyzed carbocyclization reactions for the synthesis of five- and six-membered rings.
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020 $a 9780549701828
035 $a (UMI)AAI3319834
035 $a AAI3319834
040 $a UMI $c UMI
100 1 $a Sawyer, James R. $3 1064604
245 1 0 $a Rhodium-catalyzed carbocyclization reactions for the synthesis of five- and six-membered rings.
300 $a 451 p.
500 $a Adviser: P. Andrew Evans.
500 $a Source: Dissertation Abstracts International, Volume: 69-08, Section: B, page: 4763.
502 $a Thesis (Ph.D.)--Indiana University, 2008.
520 $a Transition metal-catalyzed carbocyclization reactions are a powerful class of transformations that provide a selective and expeditious means of synthesizing target molecules by a means that is often not accessible via traditional reactions. In particular, rhodium(I) catalysts have received a significant amount of attention due to their unique reactivity in comparison to other metals.
520 $a Chapter one of this thesis describes the investigation of the rhodium-catalyzed Pauson-Khand reaction of 1,6-enyne through a collaborative effort with the Baik group. Using a combination of computational and experimental studies we have probed the origin of the diastereoselectivity that is exhibited in this reactions. Results of this work have demonstrated that the origin of the steresocontrol is significantly more complicated than a simple steric argument, with the CO pressure a choice of ligand playing a significant role. Additionally, these studies have led to the development of a room temperature carbocyclization through the incorporation of halogens a the alkyne terminus of the enyne.
520 $a Chapter two describes the discovery and development of the intermolecular rhodium-catalyzed [2+2+2] carbocyclization of enynes with alkynes. Initial studies demonstrated the ability to selectively carry out the crossed reaction through the incorporation of electron-withdrawing groups on the alkyne. This work was subsequently expanded to include the ability to control the region- and stereochemical outcome of the reaction. The Highlight of these studies was the development of a regio- and enantioselective [2+2+2] carbocyclization using methyl aryl propiolates.
520 $a Chapter three of this document outlines the initial studies toward the development of a rhodium-catalyzed [2+2+2] cycloisomerization reaction of dienynes. Optimization studies revealed that the optimum catalyst selection for this reaction was a neutral rather than cationic rhodium complex. This study delineates a highly diastereoselective intramolecular [2+2+2] cycloisomerization that offers the potential to set four contiguous stereogenic centers in a single transformation.
590 $a School code: 0093.
650 4 $a Chemistry, Inorganic. $3 517253
650 4 $a Chemistry, Organic. $3 516206
690 $a 0488
690 $a 0490
710 2 $a Indiana University. $b Chemistry. $3 1020748
773 0 $t Dissertation Abstracts International $g 69-08B.
790 $a 0093
790 1 0 $a Baik, Mu-Hyun $e committee member
790 1 0 $a Evans, P. Andrew, $e advisor
790 1 0 $a Mindiola, Daniel J. $e committee member
790 1 0 $a Williams, David R. $e committee member
791 $a Ph.D.
792 $a 2008
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3319834