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Enantioselective palladium(II) catal...

University of California, Berkeley.

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Enantioselective palladium(II) catalyzed 1,6-enyne cyclizations: Methodology development and application to total synthesis.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Enantioselective palladium(II) catalyzed 1,6-enyne cyclizations: Methodology development and application to total synthesis./
Author:	Corkey, Britton Kenneth.
Description:	261 p.
Notes:	Adviser: F. Dean Toste.
Contained By:	Dissertation Abstracts International69-10B.
Subject:	Chemistry, Inorganic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3331553
ISBN:	9780549834014

Enantioselective palladium(II) catalyzed 1,6-enyne cyclizations: Methodology development and application to total synthesis.
Corkey, Britton Kenneth.

Enantioselective palladium(II) catalyzed 1,6-enyne cyclizations: Methodology development and application to total synthesis. - 261 p.

Adviser: F. Dean Toste.

Thesis (Ph.D.)--University of California, Berkeley, 2008.

Described herein is the first enantioselective Conia-ene reaction, catalyzed by a chiral Pd(II) complex. The reaction forms products containing all-carbon quaternary stereocenters in good yield and high enantiomeric excess.

ISBN: 9780549834014Subjects--Topical Terms:

517253
Chemistry, Inorganic.

Enantioselective palladium(II) catalyzed 1,6-enyne cyclizations: Methodology development and application to total synthesis.
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020 $a 9780549834014
035 $a (UMI)AAI3331553
035 $a AAI3331553
040 $a UMI $c UMI
100 1 $a Corkey, Britton Kenneth. $3 1029794
245 1 0 $a Enantioselective palladium(II) catalyzed 1,6-enyne cyclizations: Methodology development and application to total synthesis.
300 $a 261 p.
500 $a Adviser: F. Dean Toste.
500 $a Source: Dissertation Abstracts International, Volume: 69-10, Section: B, page: 6104.
502 $a Thesis (Ph.D.)--University of California, Berkeley, 2008.
520 $a Described herein is the first enantioselective Conia-ene reaction, catalyzed by a chiral Pd(II) complex. The reaction forms products containing all-carbon quaternary stereocenters in good yield and high enantiomeric excess.
520 $a Using similar methodology, the enantioselective cyclization of silyloxy 1,6-enynes is also presented. A broad array of substrates cyclize efficiently to give products containing chiral all-carbon quaternary stereocenters in high enantiomeric excess.
520 $a A remaining challenge in the field of organic synthesis is the development of synthetic methods that form only one enantiomer of desired products. One of the most efficient and successful methods toward this end is the use of chiral catalysts to affect enantioselective organic transformations.
520 $a The application of these methods in the context of target oriented synthesis is described. Using the enantioselective cyclization of silyloxy 1,6-enynes, the first total synthesis of (-)-laurebiphenyl is accomplished. Using the analogous cyclization of enamidynes, a synthesis of the kopsifoline core is also disclosed.
520 $a Appendix A discusses attempts at rhenium catalyzed alkyne metathesis. A new rhenium-alkylidyne complex is disclosed. Appendix B presents initial results of an investigation into nickel mediated cross coupling of aryl nitriles with trimethylsilyl trifluoromethane.
590 $a School code: 0028.
650 4 $a Chemistry, Inorganic. $3 517253
650 4 $a Chemistry, Organic. $3 516206
690 $a 0488
690 $a 0490
710 2 $a University of California, Berkeley. $3 687832
773 0 $t Dissertation Abstracts International $g 69-10B.
790 $a 0028
790 1 0 $a Toste, F. Dean, $e advisor
791 $a Ph.D.
792 $a 2008
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3331553