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Enantioselective Chemo-Enzymatic Synthesis of Triaryl Phosphine Oxides and Phosphines.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Enantioselective Chemo-Enzymatic Synthesis of Triaryl Phosphine Oxides and Phosphines./
Author:	Hatton, Harry.
Published:	Ann Arbor : ProQuest Dissertations & Theses, : 2021,
Description:	233 p.
Notes:	Source: Dissertations Abstracts International, Volume: 83-04, Section: B.
Contained By:	Dissertations Abstracts International83-04B.
Subject:	Metals. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=28459562
ISBN:	9798738614576

Enantioselective Chemo-Enzymatic Synthesis of Triaryl Phosphine Oxides and Phosphines.
Hatton, Harry.

Enantioselective Chemo-Enzymatic Synthesis of Triaryl Phosphine Oxides and Phosphines. - Ann Arbor : ProQuest Dissertations & Theses, 2021 - 233 p.

Source: Dissertations Abstracts International, Volume: 83-04, Section: B.

Thesis (Ph.D.)--The University of Liverpool (United Kingdom), 2021.

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

The chemo-enzymatic synthesis of triaryl P-chiral ligands was achieved from readily available starting materials using the metallo-induced 1,4- rearrangement of phosphonates to produce pro-chiral phosphine oxides which could be enzymatically desymmetrized in good yield and high enantiomeric excess using CAL-A. The chiral phosphine oxide could then be derivatized further to produce ligand like structures. A chiral phosphine oxide could be selectively reduced to give an oxidatively stable P-chiral phosphine, with minimal loss in enantiomeric excess. Although the synthesised P-chiral ligand displayed configurational instability, slight alterations to the structure predicted by our molecular modelling results could potentially give both oxidatively and configurationally stable P-chiral phosphine ligands. Furthermore, based on unpublished results using an achiral monodentate ligand we believe that our P-chiral ligands would find application in copper-catalysed asymmetric 1,6- boration reactions with high cis selectivity.

ISBN: 9798738614576Subjects--Topical Terms:

601053
Metals.

Enantioselective Chemo-Enzymatic Synthesis of Triaryl Phosphine Oxides and Phosphines.
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245 1 0 $a Enantioselective Chemo-Enzymatic Synthesis of Triaryl Phosphine Oxides and Phosphines.
260 1 $a Ann Arbor : $b ProQuest Dissertations & Theses, $c 2021
300 $a 233 p.
500 $a Source: Dissertations Abstracts International, Volume: 83-04, Section: B.
500 $a Advisor: Carnell, Andrew.
502 $a Thesis (Ph.D.)--The University of Liverpool (United Kingdom), 2021.
506 $a This item must not be sold to any third party vendors.
520 $a The chemo-enzymatic synthesis of triaryl P-chiral ligands was achieved from readily available starting materials using the metallo-induced 1,4- rearrangement of phosphonates to produce pro-chiral phosphine oxides which could be enzymatically desymmetrized in good yield and high enantiomeric excess using CAL-A. The chiral phosphine oxide could then be derivatized further to produce ligand like structures. A chiral phosphine oxide could be selectively reduced to give an oxidatively stable P-chiral phosphine, with minimal loss in enantiomeric excess. Although the synthesised P-chiral ligand displayed configurational instability, slight alterations to the structure predicted by our molecular modelling results could potentially give both oxidatively and configurationally stable P-chiral phosphine ligands. Furthermore, based on unpublished results using an achiral monodentate ligand we believe that our P-chiral ligands would find application in copper-catalysed asymmetric 1,6- boration reactions with high cis selectivity.
590 $a School code: 0722.
650 4 $a Metals. $3 601053
650 4 $a Phosphorus. $3 671778
650 4 $a Reagents. $3 3683752
650 4 $a Biocatalysts. $3 3683849
650 4 $a Symmetry. $3 536815
650 4 $a Carbon monoxide. $3 738287
650 4 $a Hybridization. $3 1615790
650 4 $a Amino acids. $3 558768
650 4 $a Ligands. $3 686413
650 4 $a Alcohol. $3 872287
650 4 $a Chemical bonds. $3 560512
650 4 $a Energy. $3 876794
650 4 $a Green chemistry. $3 2041612
650 4 $a Ammonia. $3 2148979
650 4 $a Nickel. $3 1070054
650 4 $a Catalysis. $3 560465
650 4 $a Hydrogenation. $3 1244863
650 4 $a Enzymes. $3 520899
650 4 $a Geometry. $3 517251
650 4 $a Chemical engineering. $3 560457
650 4 $a Organic chemistry. $3 523952
650 4 $a Proteins. $3 558769
690 $a 0490
690 $a 0791
690 $a 0542
710 2 $a The University of Liverpool (United Kingdom). $3 1684840
773 0 $t Dissertations Abstracts International $g 83-04B.
790 $a 0722
791 $a Ph.D.
792 $a 2021
793 $a English
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=28459562