| Enantioselective synthesis of α-fluoro-β(3)-amino esters: synthesis of enantiopure, orthogonally protected α-fluoro-β(3)-lysine. | |
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MedLine Citation:
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PMID: 20931997 Owner: NLM Status: In-Process |
Abstract/OtherAbstract:
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The scope of a tandem conjugate addition-fluorination sequence performed on α,β-unsaturated esters using the enantiopure lithium amide derived from (S)-N-benzyl-N-(α-methylbenzyl)amine, and the electrophilic fluorinating agent N-fluorobenzenesulfonimide has been investigated. Using this method, α-fluoro-β(3)-amino esters can be obtained in up to quantitative yield and 80:20 to >99:1 dr. This simple methodology does not rely on the use of α-amino acids from the chiral pool and thus provides the potential for the preparation of enantiopure α-fluoro-β(3)-amino acids with a wide variety of side chains. Its utility was demonstrated through the synthesis of orthogonally protected (2S,3S)-α-fluoro-β(3)-lysine. |
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Authors:
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Peter J Duggan; Martin Johnston; Taryn L March |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 75 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2010 Nov |
Date Detail:
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Created Date: 2010-10-29 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 7365-72 Citation Subset: - |
Affiliation:
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CSIRO Materials Science and Engineering, Bag 10, Clayton South, Victoria 3169, Australia. peter.duggan@csiro.au |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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