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Synthesis of N-propionylated (S)-(-)-2-(pyrrolidin-2-yl)propan-2-ol and its use as a chiral auxiliary and selectivity marker in asymmetric aldol reactions
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.ORCID iD: 0000-0002-5543-2041
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Responsible organisation
2000 (English)In: Journal of the Chemical Society. Perkin Transactions 1, ISSN 1472-7781, Vol. 2000, 1513-1518 p.Article in journal (Refereed) Published
Abstract [en]

The N-propionylated pyrrolidine derivative and chiral auxiliary, (S)-(-)-2-(pyrrolidin-2-yl)propan-2-ol, was synthesised and used in stereoselective aldol reactions with benzaldehyde. Differences in stereoselectivity were investigated as a function of temperature, solvent, chelating agent and the amount of the chelating agent used by monitoring the 1H NMR spectra of the aldol adducts that were obtained. Among the additives that were investigated, Cp2ZrCl2 induced higher syn-selectivity, while SnCl2 induced higher syn-selectivity respectively. TMSCl was found to induce high selectivity for one syn- and one anti-diastereomer. Varying the ligand sets on titanium additives was found to induce differences in selectivity, with (i-PrO)3TiCl exhibiting syn-selectivity and Cp2TiCl2 exhibiting anti-selectivity. Differences in reactivity and stereoselectivity were also found to depend upon the amount of Lewis acid that was added. Methods for removal of the auxiliary were also investigated. Acidic hydrolysis was used successfully to obtain the desired 3-hydroxy-2-methyl-3-phenylpropionic acids, but was found to give low yields and resulted in a large amount of epimerisation. Furthermore, the ethyl esters of these hydroxy acids are easy to separate into pure syn- and anti-diastereomers by LC. © The Royal Society of Chemistry 2000.

Place, publisher, year, edition, pages
2000. Vol. 2000, 1513-1518 p.
Keyword [sv]
Asymmetriska reaktioner
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-2725DOI: 10.1039/b001730mISI: 000087318600007Scopus ID: 2-s2.0-0034697419Local ID: 2390OAI: oai:DiVA.org:miun-2725DiVA: diva2:27757
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-11Bibliographically approved

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CiteExportLink to record
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