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Silver-catalyzed dynamic systemic resolution of alpha-iminonitriles in a 1,3-dipolar cycloaddition process
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: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 50, no 29, 3792-3794 p.Article in journal (Refereed) Published
Abstract [en]

A dynamic azomethine ylide system was established using Sc(OTf)(3) and Ag/Taniaphos as catalysts. The system was subsequently kinetically resolved in a tandem 1,3-dipolar cycloaddition process where the silver complex acted as both a reaction catalyst and an external selector, resulting in the formation of an exclusive pyrrolidine product in good yield and enantiopurity.

Place, publisher, year, edition, pages
2014. Vol. 50, no 29, 3792-3794 p.
Keyword [en]
Combinatorial Resolution, Asymmetric-Synthesis, Azomethine Ylides, Inhibitors, Alkaloids, Transformation, Indolizidine, Derivatives, Complexes, Chemistry
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-144568DOI: 10.1039/c4cc00944dISI: 000333037000005Scopus ID: 2-s2.0-84896268279OAI: oai:DiVA.org:kth-144568DiVA: diva2:714045
Funder
Swedish Research Council
Note

QC 20140425

Available from: 2014-04-25 Created: 2014-04-24 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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