دورية أكاديمية
Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes.
| العنوان: | Copper catalyzed enantioselective intramolecular aminooxygenation of alkenes. |
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| المؤلفون: | Fuller PH; Department of Chemistry, University at Buffalo, The State University of New York, Buffalo, New York 14260, USA., Kim JW, Chemler SR |
| المصدر: | Journal of the American Chemical Society [J Am Chem Soc] 2008 Dec 31; Vol. 130 (52), pp. 17638-9. |
| نوع المنشور: | Journal Article; Research Support, N.I.H., Extramural |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 7503056 Publication Model: Print Cited Medium: Internet ISSN: 1520-5126 (Electronic) Linking ISSN: 00027863 NLM ISO Abbreviation: J Am Chem Soc Subsets: MEDLINE |
| أسماء مطبوعة: | Publication: Washington, DC : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مواضيع طبية MeSH: | Alkenes/*chemistry , Amines/*chemistry , Indoles/*chemical synthesis , Pyrrolidines/*chemical synthesis, Aniline Compounds/chemistry ; Catalysis ; Copper/chemistry ; Cyclization ; Oxidants/chemistry ; Oxidation-Reduction ; Stereoisomerism ; Sulfonamides/chemistry |
| مستخلص: | The copper-catalyzed enantioselective intramolecular aminooxygenation of alkenes is reported herein. This is the first report of an enantioselective intramolecular alkene aminooxygenation process. N-Arylsulfonyl-2-allylanilines and 4-pentenylarylsulfonamides cyclize in high yield and with good enantioselectivity, providing new chiral methyleneoxy-functionalized dihydroindolines and pyrrolidines. Tetramethylaminopyridyl radical (TEMPO) serves as both the source of the oxygen and the stoichiometric oxidant. These reactions are catalyzed by copper(II) triflate, complexed with (4S,5R)-Bis-Phbox. The unprotected aminoalcohols can be obtained by sequential dissolving metal reductions of the N-S and O-N bonds. |
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| معلومات مُعتمدة: | R01 GM078383 United States GM NIGMS NIH HHS; R01 GM078383-03 United States GM NIGMS NIH HHS |
| المشرفين على المادة: | 0 (Alkenes) 0 (Amines) 0 (Aniline Compounds) 0 (Indoles) 0 (Oxidants) 0 (Pyrrolidines) 0 (Sulfonamides) 789U1901C5 (Copper) |
| تواريخ الأحداث: | Date Created: 20081204 Date Completed: 20090126 Latest Revision: 20240511 |
| رمز التحديث: | 20240511 |
| مُعرف محوري في PubMed: | PMC2674573 |
| DOI: | 10.1021/ja806585m |
| PMID: | 19049311 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-5126 |
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| DOI: | 10.1021/ja806585m |