دورية أكاديمية
Chiral donor-acceptor azetines as powerful reactants for synthesis of amino acid derivatives.
العنوان: | Chiral donor-acceptor azetines as powerful reactants for synthesis of amino acid derivatives. |
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المؤلفون: | Marichev KO; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Dong K; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Massey LA; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Deng Y; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., De Angelis L; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Wang K; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Arman H; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA., Doyle MP; Department of Chemistry, The University of Texas at San Antonio, San Antonio, TX, 78249, USA. michael.doyle@utsa.edu. |
المصدر: | Nature communications [Nat Commun] 2019 Nov 22; Vol. 10 (1), pp. 5328. Date of Electronic Publication: 2019 Nov 22. |
نوع المنشور: | Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. |
اللغة: | English |
بيانات الدورية: | Publisher: Nature Pub. Group Country of Publication: England NLM ID: 101528555 Publication Model: Electronic Cited Medium: Internet ISSN: 2041-1723 (Electronic) Linking ISSN: 20411723 NLM ISO Abbreviation: Nat Commun Subsets: MEDLINE |
أسماء مطبوعة: | Original Publication: [London] : Nature Pub. Group |
مواضيع طبية MeSH: | Azetines/*chemical synthesis , Cycloaddition Reaction/*methods, Amino Acids ; Azetidines ; Catalysis ; Chemistry Techniques, Synthetic/methods ; Diazonium Compounds ; Indicators and Reagents/chemical synthesis ; Stereoisomerism |
مستخلص: | Coupling reactions of amines and alcohols are of central importance for applications in chemistry and biology. These transformations typically involve the use of a reagent, activated as an electrophile, onto which nucleophile coupling results in the formation of a carbon-nitrogen or a carbon-oxygen bond. Several promising reagents and procedures have been developed to achieve these bond forming processes in high yields with excellent stereocontrol, but few offer direct coupling without the intervention of a catalyst. Herein, we report the synthesis of chiral donor-acceptor azetines by highly enantioselective [3 + 1]-cycloaddition of enoldiazoacetates with aza-ylides and their selective coupling with nitrogen and oxygen nucleophiles via 3-azetidinones to form amino acid derivatives, including those of peptides and natural products. The overall process is general for a broad spectrum of nucleophiles, has a high degree of electronic and steric selectivity, and retains the enantiopurity of the original azetine. |
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المشرفين على المادة: | 0 (2-azetidinone) 0 (Amino Acids) 0 (Azetidines) 0 (Azetines) 0 (Diazonium Compounds) 0 (Indicators and Reagents) |
تواريخ الأحداث: | Date Created: 20191124 Date Completed: 20200302 Latest Revision: 20210110 |
رمز التحديث: | 20240628 |
مُعرف محوري في PubMed: | PMC6874555 |
DOI: | 10.1038/s41467-019-13326-8 |
PMID: | 31757976 |
قاعدة البيانات: | MEDLINE |
تدمد: | 2041-1723 |
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DOI: | 10.1038/s41467-019-13326-8 |