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Diastereoselective Addition of Organozinc Reagents to 2-alkyl-3-(arylsulfanyl)propanals
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
Mid Sweden University, Faculty of Science, Technology and Media, Department of Natural Sciences.
2004 (English)In: Tetrahedron, ISSN 0040-4020, E-ISSN 1464-5416, Vol. 60, no 47, 10659-10669 p.Article in journal (Refereed) Published
Abstract [en]

The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-alkyl moiety of high diastereomeric purity is described. Such compounds can serve as potential building blocks for the preparation of several kinds of natural products. Diastereoselective synthesis of two potential pine sawfly pheromone components, one the pure racemic threo-isomer of 3-methylpentadecan-2-ol and the other the racemic erythro-isomer of 3-methyltridecan-2-ol are described. The diastereoselective addition of R2Zn (R = Me, Et and n-Bu) to several 2-alkyl-3-(arylsulfanyl)propanals in the presence of a Lewis acid and CH2Cl2 as solvent was studied. An excellent diastereomeric ratio (95/5 anti-Cram/Cram) was obtained with 2-[(phenylsulfanyl)methyl]pentanal, 2-[(phenylsulfanyl)methyl]decanal and 2-[(phenylsulfanyl)methyl]dodecanal and Me2Zn in the presence of TiCl4. (C) 2004 Elsevier Ltd. All rights reserved.

Place, publisher, year, edition, pages
2004. Vol. 60, no 47, 10659-10669 p.
Keyword [en]
Dialkylzinc addition, diastereoselection, racemic 2-alkyladehydes
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-2335DOI: 10.1016/j.tet.2004.09.005ISI: 000224715100008Scopus ID: 2-s2.0-5644248089Local ID: 2196OAI: oai:DiVA.org:miun-2335DiVA: diva2:27367
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-09-23Bibliographically approved

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Larsson, MichaelHögberg, Hans-Erik
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CiteExportLink to record
Permanent link

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Cite
Citation style
  • apa
  • harvard1
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
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  • de-DE
  • en-GB
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  • fi-FI
  • nn-NO
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  • Other locale
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