| Direct mono-N-methylation of solid-supported amino acids: a useful application of the Matteson rearrangement of alpha-aminoalkylboronic esters. | |
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MedLine Citation:
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PMID: 11388848 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[reaction: see text] A novel solid-phase method for the mono-N-methylation of resin-supported amino acids was developed on the basis of Matteson's 1,2-carbon-to-nitrogen migration of boron in alpha-aminoalkylboronic esters. Amino acids supported on either Wang resin or the highly acid-sensitive SASRIN resin can be methylated by reaction with pinacol chloromethylboronic ester, followed by rearrangement of the resulting aminomethylboronate and subsequent cleavage of the boronate group. This direct method requires only a simple and expedient oxidative resin wash to repair overalkylated sites. |
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Authors:
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C Laplante; D G Hall |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Organic letters Volume: 3 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2001 May |
Date Detail:
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Created Date: 2001-06-04 Completed Date: 2001-12-04 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 1487-90 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Alberta, Edmonton AB, Canada T6G 2G2. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Amino Acids
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chemical synthesis*,
chemistry Combinatorial Chemistry Techniques / methods* Magnetic Resonance Spectroscopy Methylation Resins, Plant |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Resins, Plant |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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