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Direct Catalytic Asymmetric Synthesis of Pyrazolidine Derivatives
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Stockholms universitet, Naturvetenskapliga fakulteten, Institutionen för organisk kemi.
Visa övriga samt affilieringar
2012 (Engelska)Ingår i: ChemistryOpen, ISSN 2191-1363, Vol. 1, nr 3, s. 134-139Artikel i tidskrift (Refereegranskat) Published
Abstract [en]

A highly enantioselective, metal-free cascade reaction between di-1,2-N-protected hydrazine and α,β-unsaturated aldehydes is disclosed. The catalytic, asymmetric cascade transformation is a direct entry to 3-hydroxypyrazolidine and 3-allylpyrazolidine derivatives in one step and two steps, respectively, with >19:1 d.r. and 98–99 % ee using simple chiral pyrrolidines as catalysts.

Ort, förlag, år, upplaga, sidor
2012. Vol. 1, nr 3, s. 134-139
Nyckelord [en]
1, 4-selectivity, asymmetric catalysis, cascade reactions, hemiaminals, metal-free catalysis, pyrazolidines
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
URN: urn:nbn:se:su:diva-94675DOI: 10.1002/open.201200015OAI: oai:DiVA.org:su-94675DiVA, id: diva2:654792
Tillgänglig från: 2013-10-08 Skapad: 2013-10-08 Senast uppdaterad: 2017-12-06Bibliografiskt granskad
Ingår i avhandling
1. Development of Catalytic Enantioselective Approaches for the Synthesis of Carbocycles and Heterocycles
Öppna denna publikation i ny flik eller fönster >>Development of Catalytic Enantioselective Approaches for the Synthesis of Carbocycles and Heterocycles
2013 (Engelska)Doktorsavhandling, sammanläggning (Övrigt vetenskapligt)
Abstract [en]

In biological systems, most of the active organic molecules are chiral. Some of the main constituents of living organisms are amino acids and sugars. They exist predominantly in only one enantiomerically pure form. For example, our proteins are built-up by L-amino acids and as a consequence they are enatiomerically pure and will interact in different ways with enantiomers of chiral molecules. Indeed, different enantiomers or diastereomers of a molecule could often have a drastically different biological activity. It is of paramount importance in organic synthesis to develop new routes to control and direct the stereochemical outcome of reactions. The aim of this thesis is to investigate new protocols for the synthesis of complex chiral molecules using simple, environmentally friendly proline-based organocatalysts. We have investigated, the aziridination of linear and branched enals, the stereoselective synthesis of β-amino acids with a carbene co-catalyst, the synthesis of pyrazolidines, the combination of heterogeneous transition metal catalysis and amine catalysis to deliver cyclopentenes bearing an all-carbon quaternary stereocenter and a new heterogeneous dual catalyst system for the carbocyclization of enals. The reactions presented in this thesis afforded the corresponding products with high levels of chemo-, diastero- and enantioselectivity.

Ort, förlag, år, upplaga, sidor
Stockholm: Department of Organic Chemistry, Stockholm University, 2013. s. 75
Nyckelord
Organocatalysis, Asymmetric Catalysis, Heterogeneous Catalysis, Aziridines, Pyrazolidines, Cyclopentanes
Nationell ämneskategori
Organisk kemi
Forskningsämne
organisk kemi
Identifikatorer
urn:nbn:se:su:diva-94680 (URN)978-91-7447-781-8 (ISBN)
Disputation
2013-12-04, Magnélisalen, Kemiska övningslaboratoriet, Svante Arrhenius väg 16 B, Stockholm, 10:00 (Engelska)
Opponent
Handledare
Anmärkning

At the time of the doctoral defense, the following paper was unpublished and had a status as follows: Paper 5: Submitted. 

Tillgänglig från: 2013-11-12 Skapad: 2013-10-08 Senast uppdaterad: 2014-09-24Bibliografiskt granskad

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Deiana, LucaSun, JunliangCórdova, Armando
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Institutionen för organisk kemiAvdelningen för strukturkemi
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