| Enantioselective alpha-silyl amino acid synthesis by reverse-aza-Brook rearrangement. | |
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MedLine Citation:
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PMID: 14627413 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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[reaction: see text] Asymmetric reverse-aza-Brook rearrangement of N-Boc-N-trialkylsilyl allylamine yields an enantiomerically enriched alpha-amino allylsilane. Oxidative cleavage of the alkene leads to a Boc-protected amino acid with the configuration of naturally occurring amino acids (L). Standard coupling protocols, including the use of trifluoroacetic acid for removal of the Boc group, yield a tripeptide with a central silane amino acid. |
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Authors:
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Guodong Liu; Scott McN Sieburth |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, P.H.S. |
Journal Detail:
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Title: Organic letters Volume: 5 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2003 Nov |
Date Detail:
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Created Date: 2003-11-20 Completed Date: 2004-05-24 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: 4677-9 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19122, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Allylamine
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chemistry Amino Acids / chemical synthesis*, chemistry* Molecular Structure Oxidation-Reduction Peptides / chemical synthesis*, chemistry Silanes / chemistry* Stereoisomerism Trifluoroacetic Acid / chemistry |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Peptides; 0/Silanes; 107-11-9/Allylamine; 76-05-1/Trifluoroacetic Acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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