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Crystallization-induced secondary selection from a tandem driven dynamic combinatorial resolution process
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.
2008 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 73, no 9, 3593-3595 p.Article in journal (Refereed) Published
Abstract [en]

Crystallization-induced secondary selection from a tandem driven dynamic combinatorial library is presented. In a one-pot experiment, an initial nitroaldol equilibrium was kinetically driven by a tandem reaction resulting in a subsequent dynamic library of diastereoisomers. This library was then further driven by a phase change, resulting in amplification and isolation of a highly diastereomerically enriched and synthetically interesting isoindolinone.

Place, publisher, year, edition, pages
2008. Vol. 73, no 9, 3593-3595 p.
Keyword [en]
ASYMMETRIC-SYNTHESIS, DRUG DISCOVERY, SOLID-STATE, CHEMISTRY, LIBRARIES, REARRANGEMENT, LIGANDS
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-12713ISI: 000255339600042Scopus ID: 2-s2.0-43449087343OAI: oai:DiVA.org:kth-12713DiVA: diva2:318259
Note

QC 20100507

Available from: 2010-05-07 Created: 2010-05-07 Last updated: 2017-04-28Bibliographically approved
In thesis
1. Discovery-Oriented Screening of Dynamic Systems: Combinatorial and Synthetic Applications
Open this publication in new window or tab >>Discovery-Oriented Screening of Dynamic Systems: Combinatorial and Synthetic Applications
2010 (English)Doctoral thesis, comprehensive summary (Other academic)
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.

Place, publisher, year, edition, pages
Stockholm: KTH, 2010. 82 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2010:13
Keyword
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
National Category
Organic Chemistry Organic Chemistry
Identifiers
urn:nbn:se:kth:diva-12524 (URN)978-91-7415-617-1 (ISBN)
Public defence
2010-05-28, F3, Lindstedtsvägen 26, KTH, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20100628Available from: 2010-05-12 Created: 2010-05-03 Last updated: 2011-02-11Bibliographically approved

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