| Synthesis of orthogonally protected biaryl amino acid derivatives. | |
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MedLine Citation:
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PMID: 16990939 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The efficient and direct synthesis of protected biaryl amino acids, including dityrosine (50% overall yield over 3 steps), by Negishi cross-coupling of the serine-derived organozinc reagent 4 with iodo- and di-iodobiaryls, is reported. An improved, although still not perfect, diiodination of 2,2'-biphenol has been achieved using NMe3BnICl2-ZnCl2. Protection of phenolic hydroxyl groups as acetates, rather than benzyl ethers, is required for efficient cross-coupling, and evidence for acetyl migration has been observed during debenzylation of a substituted 2-acetoxy-2'-benzyloxybiaryl. Aromatic C-I to C-Cl conversion has been detected as a minor reaction pathway in the palladium-catalyzed coupling of aryl iodide 3b with organozinc reagent 4. |
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Authors:
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Eduardo Moreno; Luca Antonio Nolasco; Lorenzo Caggiano; Richard F W Jackson |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2006-08-23 |
Journal Detail:
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Title: Organic & biomolecular chemistry Volume: 4 ISSN: 1477-0520 ISO Abbreviation: Org. Biomol. Chem. Publication Date: 2006 Oct |
Date Detail:
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Created Date: 2006-09-22 Completed Date: 2007-08-28 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 101154995 Medline TA: Org Biomol Chem Country: England |
Other Details:
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Languages: eng Pagination: 3639-47 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Dainton Building, University of Sheffield, Brook Hill, Sheffield, UK S3 7HF. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemical synthesis*,
chemistry* Catalysis Palladium / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 7440-05-3/Palladium |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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