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Diastereoselective Addition of Methylmetallic Reagents to 2-Methylaldehydes
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.
2001 (English)In: Tetrahedron, ISSN 0040-4020, Vol. 57, no 35, 7541-7548 p.Article in journal (Refereed) Published
Abstract [en]

The preparation of compounds incorporating the 3-hydroxy-2-methyl-1-butyl moiety of high diastereomeric purity is described. These compounds can serve as potential building blocks for the preparation of several kinds of natural products. The diastereoselective addition of a number of methylmetal derivatives to three 3-substituted 2-methylaldehydes in various solvents was studied. An excellent diastereomeric ratio (95:5 anti-Cram/Cram) was obtained with 2-methyl-3-(phenylsulfanyl)propanal (5) and Me2Zn in the presence of TiCl4.

Place, publisher, year, edition, pages
2001. Vol. 57, no 35, 7541-7548 p.
Keyword [en]
asymmetric induction, diastereoselection, chelation
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:miun:diva-2167DOI: 10.1016/S0040-4020(01)00713-XISI: 000170631700013Scopus ID: 2-s2.0-0035959454Local ID: 1246OAI: oai:DiVA.org:miun-2167DiVA: diva2:27199
Available from: 2008-09-30 Created: 2008-09-30 Last updated: 2016-10-17Bibliographically approved

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CiteExportLink to record
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