| Catalytic α-Allylation of Unprotected Amino Acid Esters. | |
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MedLine Citation:
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PMID: 22486157 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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Catalytic α-allylation of unprotected amino acid esters to produce α-quaternary α-allyl amino acid esters is reported. Catalytic loadings of picolinaldehyde and Ni(II) salts induce preferential reactivity at the enolizable α-carbon of amino acid esters over the free nitrogen with electrophilic palladium π-allyl complexes. Fourteen examples are given. Additionally, the use of chiral ligands to access enantioenriched α-quaternary amino acid esters from racemic precursors is demonstrated by the enantioselective synthesis of α-allyl phenylalanine methyl ester from racemic phenylalanine methyl ester. |
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Authors:
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Ping Fang; Mani Raj Chaulagain; Zachary D Aron |
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Publication Detail:
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Type: JOURNAL ARTICLE Date: 2012-4-9 |
Journal Detail:
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Title: Organic letters Volume: - ISSN: 1523-7052 ISO Abbreviation: - Publication Date: 2012 Apr |
Date Detail:
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Created Date: 2012-4-10 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: - |
Other Details:
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Languages: ENG Pagination: - Citation Subset: - |
Affiliation:
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Department of Chemistry, Indiana University, 800 East Kirkwood Avenue, Bloomington, Indiana 47405-7102, United States. |
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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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