| Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acids via P-C bond formation and hydrogenation. | |
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MedLine Citation:
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PMID: 17691799 Owner: NLM Status: PubMed-not-MEDLINE |
Abstract/OtherAbstract:
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Allylic acetates, formed by the acetylation of Baylis Hillman adducts, undergo addition of phosphorus nucleophiles to give stereoselectively the Z-unsaturated esters. TFA cleavage of the tert-butyl ester and asymmetric hydrogenation of the unsaturated acid yields the phosphono alkyl propanoic acid moiety, commonly found in phosphonate- and phosphinate-based enzyme inhibitors. |
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Authors:
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Pallavi A Badkar; Nigam P Rath; Christopher D Spilling |
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Publication Detail:
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Type: Journal Article Date: 2007-08-11 |
Journal Detail:
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Title: Organic letters Volume: 9 ISSN: 1523-7060 ISO Abbreviation: Org. Lett. Publication Date: 2007 Aug |
Date Detail:
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Created Date: 2007-08-23 Completed Date: 2007-11-09 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: 3619-22 Citation Subset: - |
Affiliation:
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Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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