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Enantioselective synthesis of m-carboranylalanine, a boron-rich analogue of phenylalanine
Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
Uppsala University, Teknisk-naturvetenskapliga vetenskapsområdet, Chemistry, Department of Chemistry. Department of Biochemistry and Organic Chemistry, Organic Chemistry II. Organisk kemi.
2005 (English)In: Tetrahedron, Vol. 61, 1181-1186 p.Article in journal (Refereed) Published
Abstract [en]

The enantiomers of the highly lipophilic a-amino acid m-carboranyl-alanine [3-(1.7-dicarba-closo-dodecaborane(12)-1-yl)-2-aminopropanoic acid], a carborane containing analogue of phenylalanine, have been synthesised via hydroxyamination of the N-acyl derivative formed from 3-(m-carboranyl)propionoic acid [3-(1.7-dicarba-closo-dodeca-borane(12)-1-yl)-2-propanoic acid] and Oppolzer's camphor sultam. The enantiomeric excess of both enantiomers of the amino acid was >98%. (S)-Configuration was assigned to the (+)-enantiomer (ch3Oh, 589 nm).

Place, publisher, year, edition, pages
2005. Vol. 61, 1181-1186 p.
Keyword [en]
m-Carboranylalanine, Absolute configuration, Carborane, Boron neutron capture therapy, Asymmetric synthesis, Highly lipophilic amino acid
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-70005DOI: doi:10.1016/j.tet.2004.11.045OAI: oai:DiVA.org:uu-70005DiVA: diva2:97916
Available from: 2005-04-13 Created: 2005-04-13 Last updated: 2011-01-12

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Sjöberg, Stefan

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