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(S)-1,2,3,4-tetrahydroisoquinoline derived chiral auxiliary in diastereoselective alkylation
Mid Sweden University, Faculty of Science, Technology and Media, Department of Chemical Engineering.
(English)Manuscript (preprint) (Other academic)
Abstract [en]

A novel chiral auxiliary (S)-2-(1,2,3,4-tetrahydroisoquinolin-3-yl)propan-2-ol 1 was synthesized from (S)-1,2,3,4-tetrahydroisoquinoline acid 2. Alkylation of the propanoylated chiral auxiliary (S)-1-(3-(2-hydroxypropan-2-yl)-3,4-dihydroisoquinolin-2(1H)-yl)-propan-1-one 3 with benzyl bromide or n-butyl iodide caused moderate to high conversion (42–99%) and moderate diastereomeric ratios (up to 89:11). The major diastereomer obtained in the reaction with benzyl bromide was (R,S). Some of the reactions were carried out with LiCl as an enolate coordinating agent, which affected conversion and diastereomeric ratio negatively. 

Keyword [en]
chiral auxiliary, diastereomer, tetrahydroisoquinoline, alkylation
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:miun:diva-24597OAI: oai:DiVA.org:miun-24597DiVA: diva2:795888
Available from: 2015-03-17 Created: 2015-03-17 Last updated: 2015-04-14Bibliographically approved

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Sjöberg, Natalia
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Department of Chemical Engineering
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