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Lipase-catalyzed asymmetric synthesis of oxathiazinanones through dynamic covalent kinetic resolution
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
KTH, School of Chemical Science and Engineering (CHE), Chemistry, Organic Chemistry.
2014 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 12, no 22, 3572-3575 p.Article in journal (Refereed) Published
Abstract [en]

A domino addition-lactonization pathway has been applied to a dynamic covalent resolution protocol, leading to efficient oxathiazinanone formation as well as chiral discrimination. A new, double biocatalytic pathway has furthermore been proposed and evaluated where the initial product inhibition could be efficiently circumvented.

Place, publisher, year, edition, pages
2014. Vol. 12, no 22, 3572-3575 p.
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-147756DOI: 10.1039/c4ob00365aISI: 000336782000006Scopus ID: 2-s2.0-84900819904OAI: oai:DiVA.org:kth-147756DiVA: diva2:732401
Funder
Swedish Research Council
Note

QC 20140704

Available from: 2014-07-04 Created: 2014-07-03 Last updated: 2017-12-05Bibliographically approved
In thesis
1. Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
Open this publication in new window or tab >>Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
2014 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

This thesis is built on the concepts of constitutional dynamic chemistry and dynamic kinetic resolution, where reversible covalent reactions are used to generate dynamics and kinetically controlled reactions are employed for resolution. The thesis is divided into two parts:

The first section focuses on the study of dynamic systemic resolution, a concept derived from constitutional dynamic chemistry. Three projects are addressed in this section: 1) lipase-catalyzed resolution of a double parallel dynamic system involving both hemiacetal formation and nitroaldol reaction; 2) resolution of a dynamic α-iminonitrile system through a silver-catalyzed 1,3-dipolar cycloaddition process; 3) resolution of a dynamic imine system via organogelation. Both external and internal selection pressures are applied for the resolution of complex dynamic systems.

The second section explores the asymmetric synthesis of two types of heterocycles through dynamic kinetic resolution. In the first example, a series of novel N-, O-, S-containing six-membered oxathiazinanones are obtained through a lipase-mediated dynamic domino nitrone addition-cyclization pathway. In the second example, the anti-HIV nucleoside lamivudine is synthesized through a three-step surfactant-treated subtilisin Carlsberg-catalyzed dynamic kinetic resolution protocol. Its enantiomer is also accessible by changing subtilisin Carlsberg to lipases. In addition, the enzyme selectivity towards the formation of five-membered oxathiolane derivatives is investigated.

Place, publisher, year, edition, pages
Stockholm: KTH Royal Institute of Technology, 2014. 63 p.
Series
TRITA-CHE-Report, ISSN 1654-1081 ; 2014:34
National Category
Organic Chemistry
Research subject
Chemistry
Identifiers
urn:nbn:se:kth:diva-151314 (URN)978-91-7595-239-0 (ISBN)
Public defence
2014-10-10, F3, Lindstedtsvägen 26, KTH, Stockholm, 14:00 (English)
Opponent
Supervisors
Funder
Swedish Research Council, KDHH B60940
Note

QC 20140918

Available from: 2014-09-18 Created: 2014-09-17 Last updated: 2014-09-18Bibliographically approved

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