| A formal enantioselective acetate Mannich reaction: the nitro functional group as a traceless agent for activation and enantiocontrol in the synthesis of beta-amino acids. | |
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MedLine Citation:
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PMID: 18798639 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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A two-step procedure involving the enantioselective addition of alpha-nitro esters to imines, followed by reductive denitration, provides a convenient new enantioselective synthesis of beta-amino acids. Specifically, beta-phenyl alanine derivatives with up to 98% ee are formed in good yield (64-88%) over two steps. The utility of the approach is demonstrated through the first enantioselective synthesis of the key beta-amino acid of (+)-chaenorhine. |
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Authors:
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Bo Shen; Jeffrey N Johnston |
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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, Non-P.H.S. Date: 2008-09-18 |
Journal Detail:
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Title: Organic letters Volume: 10 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2008 Oct |
Date Detail:
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Created Date: 2008-10-09 Completed Date: 2008-12-10 Revised Date: - |
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: 4397-400 Citation Subset: IM |
Affiliation:
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Department of Chemistry & Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235-1822, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acetates
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chemistry* Amino Acids / chemical synthesis*, chemistry Catalysis Esters / chemistry Mannich Bases / chemistry Molecular Structure Nitrogen Compounds / chemistry* Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Acetates; 0/Amino Acids; 0/Esters; 0/Mannich Bases; 0/Nitrogen Compounds |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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