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Silver-catalyzed dynamic systemic resolution of alpha-iminonitriles in a 1,3-dipolar cycloaddition process
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
2014 (Engelska)Ingår i: Chemical Communications, ISSN 1359-7345, E-ISSN 1364-548X, Vol. 50, nr 29, s. 3792-3794Artikel i tidskrift (Refereegranskat) 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.

Ort, förlag, år, upplaga, sidor
2014. Vol. 50, nr 29, s. 3792-3794
Nyckelord [en]
Combinatorial Resolution, Asymmetric-Synthesis, Azomethine Ylides, Inhibitors, Alkaloids, Transformation, Indolizidine, Derivatives, Complexes, Chemistry
Nationell ämneskategori
Organisk kemi
Identifikatorer
URN: urn:nbn:se:kth:diva-144568DOI: 10.1039/c4cc00944dISI: 000333037000005Scopus ID: 2-s2.0-84896268279OAI: oai:DiVA.org:kth-144568DiVA, id: diva2:714045
Forskningsfinansiär
Vetenskapsrådet
Anmärkning

QC 20140425

Tillgänglig från: 2014-04-25 Skapad: 2014-04-24 Senast uppdaterad: 2017-12-05Bibliografiskt granskad
Ingår i avhandling
1. Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
Öppna denna publikation i ny flik eller fönster >>Resolution of Dynamic Systems: Applications in Asymmetric Synthesis and Materials Science
2014 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
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.

Ort, förlag, år, upplaga, sidor
Stockholm: KTH Royal Institute of Technology, 2014. s. 63
Serie
TRITA-CHE-Report, ISSN 1654-1081 ; 2014:34
Nationell ämneskategori
Organisk kemi
Forskningsämne
Kemi
Identifikatorer
urn:nbn:se:kth:diva-151314 (URN)978-91-7595-239-0 (ISBN)
Disputation
2014-10-10, F3, Lindstedtsvägen 26, KTH, Stockholm, 14:00 (Engelska)
Opponent
Handledare
Forskningsfinansiär
Vetenskapsrådet, KDHH B60940
Anmärkning

QC 20140918

Tillgänglig från: 2014-09-18 Skapad: 2014-09-17 Senast uppdaterad: 2014-09-18Bibliografiskt granskad

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