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Crystallization Driven Asymmetric Synthesis of Pyridine β-Nitroalcoholsvia Discovery-Oriented Self-Resolution of a Dynamic System
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
KTH, Skolan för kemivetenskap (CHE), Kemi, Organisk kemi.
2010 (engelsk)Inngår i: European Journal of Organic Chemistry, ISSN 1434-193X, E-ISSN 1099-0690, Vol. 33, s. 6315-6318Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

The study of dynamic nitroaldol systems aided the discovery of a diastereoselective crystallization process through amplification of 2-nitro-1-(pyridine-4-yl)propan-1-ol. The phenomenon was further developed into an effective procedure for asymmetic synthesis of pyridine-nitroalcohols and several substrates were screened to this end. These results demonstrate how work with larger dynamic systems facilitates and increases the likelihood of serendipitous discoveries.

sted, utgiver, år, opplag, sider
2010. Vol. 33, s. 6315-6318
Emneord [en]
Dynamic combinatorial chemistry, Systems chemistry, Aldol reactions, Asymmetric synthesis, Crystallization
HSV kategori
Identifikatorer
URN: urn:nbn:se:kth:diva-13741DOI: 10.1002/ejoc.201000907ISI: 000285229700002Scopus ID: 2-s2.0-78649310287OAI: oai:DiVA.org:kth-13741DiVA, id: diva2:327066
Forskningsfinansiär
Swedish Research Council
Merknad
Updated from submitted to published. QC 20120326Tilgjengelig fra: 2010-06-28 Laget: 2010-06-28 Sist oppdatert: 2017-12-12bibliografisk kontrollert
Inngår i avhandling
1. Discovery-Oriented Screening of Dynamic Systems: Combinatorial and Synthetic Applications
Åpne denne publikasjonen i ny fane eller vindu >>Discovery-Oriented Screening of Dynamic Systems: Combinatorial and Synthetic Applications
2010 (engelsk)Doktoravhandling, med artikler (Annet vitenskapelig)
Abstract [en]

This thesis is divided into six parts, all centered around the development of dynamic (i.e., reversibly interacting) systems of molecules and their applications in dynamic combinatorial chemistry (DCC) and organic synthesis.

Part one offers a general introduction, as well as a more detailed description of DCC, being the central concept of this thesis. Part two explores the potential of the nitroaldol reaction as a tool for constructing dynamic systems, employing benzaldehyde derivatives and nitroalkanes. This reaction is then applied in part three where a dynamic nitroaldol system is resolved by lipase-catalyzed transacylation, selecting two out of 16 components.

In part four, reaction and crystallization driven DCC protocols are developed and demonstrated. The discovery of unexpected crystalline properties of certain pyridine β-nitroalcohols is used to resolve a dynamic system and further expanded into asynthetic procedure. Furthermore, a previously unexplored tandem nitroaldol-iminolactone rearrangement reaction between 2-cyanobenzaldehyde and primarynitroalkanes is used for the resolution of dynamic systems. It is also coupled with diastereoselective crystallization to demonstrate the possibility to combine several selection processes. The mechanism of this reaction is investigated and a synthetic protocol is developed for asymmetric synthesis of 3-substituted isoindolinones.

Part five continues the exploration of tandem reactions by combining dynamic hemithioacetal or cyanohydrin formation with intramolecular cyclization to synthesize a wide range of 3-functionalized phthalides.

Finally, part six deals with the construction of a laboratory experiment to facilitate the introduction of DCC in undergraduate chemistry education. The experiment is based on previous work in our group and features an acetylcholinesterase-catalyzed resolution of a dynamic transthioacylation system.

sted, utgiver, år, opplag, sider
Stockholm: KTH, 2010. s. 82
Serie
Trita-CHE-Report, ISSN 1654-1081 ; 2010:13
Emneord
chemical education, crystallization, dynamic combinatorial chemistry, dynamic combinatorial resolution, dynamic system, enzyme catalysis, isoindolinone, lipase, nitroalcohol, nitroaldol reaction, phthalide, reversible, secondary alcohol, systems chemistry, tandem reaction
HSV kategori
Identifikatorer
urn:nbn:se:kth:diva-12524 (URN)978-91-7415-617-1 (ISBN)
Disputas
2010-05-28, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (engelsk)
Opponent
Veileder
Merknad
QC 20100628Tilgjengelig fra: 2010-05-12 Laget: 2010-05-03 Sist oppdatert: 2011-02-11bibliografisk kontrollert

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