دورية أكاديمية
Enantioselective Synthesis of 3,3-Difluoropyrrolidin-4-ol, a Valuable Building Block in Medicinal Chemistry.
| العنوان: | Enantioselective Synthesis of 3,3-Difluoropyrrolidin-4-ol, a Valuable Building Block in Medicinal Chemistry. |
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| المؤلفون: | Si C; DCR&T, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, United States., Fales KR; DCR&T, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, United States., Torrado A; DCR&T, Lilly Spain S.A., Avda de la Industria 30, Alcobendas Madrid, 28108, Spain., Frimpong K; DCR&T, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, United States., Kaoudi T; DCR&T, Lilly Spain S.A., Avda de la Industria 30, Alcobendas Madrid, 28108, Spain., Vandeveer HG; AMRI, 26 Corporate Circle, Albany, New York 12203, United States., Njoroge FG; DCR&T, Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 46285, United States. |
| المصدر: | The Journal of organic chemistry [J Org Chem] 2016 May 20; Vol. 81 (10), pp. 4359-63. Date of Electronic Publication: 2016 May 10. |
| نوع المنشور: | Journal Article |
| اللغة: | English |
| بيانات الدورية: | Publisher: American Chemical Society Country of Publication: United States NLM ID: 2985193R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1520-6904 (Electronic) Linking ISSN: 00223263 NLM ISO Abbreviation: J Org Chem Subsets: PubMed not MEDLINE |
| أسماء مطبوعة: | Publication: Columbus Oh : American Chemical Society Original Publication: Easton, Pa. [etc.] |
| مستخلص: | In this paper, we report for the first time two enantioselective routes to 4,4-difluoropyrrolidin-3-ol, a valuable building block in medicinal chemistry. In the first route, we took advantage of the C2 symmetry of (3R,4R)-3,4-dihydroxypyrrolidine in which the desired chirality was derived from the chiral pool (l-(+)-tartaric acid). In the second route, we efficiently assembled the pyrrolidine ring in the presence of a gem-difluoro moiety to avoid using potentially hazardous deoxofluorinating reagents and subsequently introduced the chirality by a stereoselective iridium-diamine-catalyzed asymmetric transfer hydrogenation reaction. |
| تواريخ الأحداث: | Date Created: 20160504 Date Completed: 20180516 Latest Revision: 20180516 |
| رمز التحديث: | 20231215 |
| DOI: | 10.1021/acs.joc.6b00305 |
| PMID: | 27138111 |
| قاعدة البيانات: | MEDLINE |
Find this issue from the American Chemical Society | تدمد: | 1520-6904 |
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| DOI: | 10.1021/acs.joc.6b00305 |