Enantioselective Synthesis of α-Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of -Butyl ((1 )-1-(4-(benzyloxy)phenyl)-2-bromo-2-nitroethyl)carbamate.
作者信息
Lim Victoria T, Tsukanov Sergey V, Stephens Amanda B, Johnston Jeffrey N
机构信息
Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, Tennessee 37235.
出版信息
Organic Synth. 2016;93:88-99. doi: 10.15227/orgsyn.093.0088.
Abstract
摘要
相似文献
1
Enantioselective Synthesis of α-Bromonitroalkanes for Umpolung Amide Synthesis: Preparation of
-Butyl ((1
)-1-(4-(benzyloxy)phenyl)-2-bromo-2-nitroethyl)carbamate.用于极性反转酰胺合成的α-溴代硝基烷烃的对映选择性合成：（1S）-丁基（（1）-1-（4-（苄氧基）苯基）-2-溴-2-硝基乙基）氨基甲酸酯的制备
Organic Synth. 2016;93:88-99. doi: 10.15227/orgsyn.093.0088.
2
Enantioselective synthesis of α-oxy amides via Umpolung amide synthesis.通过反转酰胺合成反应进行α-氧代酰胺的对映选择性合成。
J Am Chem Soc. 2012 Sep 19;134(37):15233-6. doi: 10.1021/ja306225u. Epub 2012 Sep 11.
3
Novel synthesis of 5-amino-3-bromo-1-(tert-butyl)-1H-pyrazole-4-carbonitrile: a versatile intermediate for the preparation of 5-amino-3-aryl-1-(tert-butyl)-1H-pyrazole-4-carboxamides.新型合成 5-氨基-3-溴-1-(叔丁基)-1H-吡唑-4-甲腈：一种用于制备 5-氨基-3-芳基-1-(叔丁基)-1H-吡唑-4-甲酰胺的多功能中间体。
Org Lett. 2012 Aug 3;14(15):3906-8. doi: 10.1021/ol301655f. Epub 2012 Jul 18.
4
Umpolung amide synthesis using substoichiometric N-iodosuccinimide (NIS) and oxygen as a terminal oxidant.使用化学计量比以下的N-碘代琥珀酰亚胺（NIS）和氧气作为终端氧化剂的极性反转酰胺合成。
Org Lett. 2014 Sep 19;16(18):4714-7. doi: 10.1021/ol502089v. Epub 2014 Sep 8.
5
An efficient and scalable Ritter reaction for the synthesis of tert-butyl amides.一种高效且可扩展的 Ritter 反应，用于合成叔丁酰胺。
J Org Chem. 2009 Mar 6;74(5):2207-9. doi: 10.1021/jo8024797.
6
Carbamoyl translocations by an anionic ortho-fries and cumulenolate alpha-acylation pathway: regioselective synthesis of polysubstituted chromone 3- and 8-carboxamides.通过阴离子邻位弗里斯重排和累积烯醇酸酯α-酰化途径进行的氨基甲酰基迁移：多取代色酮3-和8-羧酰胺的区域选择性合成
Angew Chem Int Ed Engl. 2008;47(11):2097-101. doi: 10.1002/anie.200704360.
7
Protecting group-free method for synthesis of N-glycosyl carbamates and an assessment of the anomeric effect of nitrogen in the carbamate group.无保护基合成 N-糖基氨基甲酸酯的方法及氨基甲酸酯中氮原子的变旋作用研究。
Carbohydr Res. 2021 Jul;505:108280. doi: 10.1016/j.carres.2021.108280. Epub 2021 Mar 7.
8
Discovery of competing anaerobic and aerobic pathways in umpolung amide synthesis allows for site-selective amide 18O-labeling.在反转酰胺合成中发现竞争的厌氧和需氧途径，允许进行位点选择性酰胺 18O 标记。
Proc Natl Acad Sci U S A. 2012 Jan 3;109(1):44-6. doi: 10.1073/pnas.1113553108. Epub 2011 Dec 19.
9
Aqueous phosphoric acid as a mild reagent for deprotection of tert-butyl carbamates, esters, and ethers.磷酸水溶液作为一种用于脱除叔丁基氨基甲酸酯、酯和醚保护基的温和试剂。
J Org Chem. 2006 Nov 24;71(24):9045-50. doi: 10.1021/jo061377b.
10
Novel C-3 N-urea, amide, and carbamate dihydroindazolo[5,4-a]pyrrolo[3,4-c]carbazole analogs as potent TIE-2 and VEGF-R2 dual inhibitors.新型C-3 N-脲、酰胺和氨基甲酸酯二氢吲唑并[5,4-a]吡咯并[3,4-c]咔唑类似物作为有效的TIE-2和VEGF-R2双重抑制剂。
Bioorg Med Chem Lett. 2006 Oct 15;16(20):5368-72. doi: 10.1016/j.bmcl.2006.07.066. Epub 2006 Aug 4.
引用本文的文献
1
Total Synthesis of Feglymycin Using Umpolung Amide Synthesis.利用极性反转酰胺合成法全合成费格霉素
Angew Chem Int Ed Engl. 2025 Sep 8;64(37):e202508819. doi: 10.1002/anie.202508819. Epub 2025 Jul 26.
2
Preparation of -Aryl Amides by Epimerization-Free Umpolung Amide Synthesis.通过非对映反转酰胺合成制备 -芳基酰胺。
J Am Chem Soc. 2022 Sep 21;144(37):16708-16714. doi: 10.1021/jacs.2c05986. Epub 2022 Sep 6.
3
Resolving Bromonitromethane Sourcing by Synthesis: Preparation at the Decagram Scale.通过合成解决溴硝基甲烷的来源问题：以十克规模进行制备。
J Org Chem. 2022 Apr 15;87(8):5451-5455. doi: 10.1021/acs.joc.2c00405. Epub 2022 Apr 1.
4
Fluorine-induced diastereodivergence discovered in an equally rare enantioselective -aza-Henry reaction.在同样罕见的对映选择性氮杂-Henry反应中发现氟诱导的非对映选择性差异。
Chem Sci. 2022 Feb 14;13(9):2614-2623. doi: 10.1039/d1sc05910f. eCollection 2022 Mar 2.
5
The inverted ketene synthon: a double umpolung approach to enantioselective β-amino amide synthesis.内酮烯合成子：一种用于对映选择性β-氨基酰胺合成的双重极性翻转方法。
Chem Sci. 2018 Nov 12;10(4):1138-1143. doi: 10.1039/c8sc04330b. eCollection 2019 Jan 28.
6
A convergent synthesis of 1,3,4-oxadiazoles from acyl hydrazides under semiaqueous conditions.在半水相条件下由酰肼合成1,3,4-恶二唑的汇聚式合成法。
Chem Sci. 2017 Apr 1;8(4):3187-3191. doi: 10.1039/c7sc00195a. Epub 2017 Feb 23.
本文引用的文献
1
Preparation of H,(4) PyrrolidineQuin-BAM (PBAM).H,(4) 吡咯烷喹啉 - BAM（PBAM）的制备。
Organic Synth. 2012;89:380-393. doi: 10.15227/orgsyn.089.0380. Epub 2012 Feb 22.
2
Rethinking amide bond synthesis.重新思考酰胺键的合成。
Nature. 2011 Dec 21;480(7378):471-9. doi: 10.1038/nature10702.
3
Discovery of competing anaerobic and aerobic pathways in umpolung amide synthesis allows for site-selective amide 18O-labeling.在反转酰胺合成中发现竞争的厌氧和需氧途径，允许进行位点选择性酰胺 18O 标记。
Proc Natl Acad Sci U S A. 2012 Jan 3;109(1):44-6. doi: 10.1073/pnas.1113553108. Epub 2011 Dec 19.
4
Umpolung reactivity in amide and peptide synthesis.酰胺和肽合成中的反转反应性。
Nature. 2010 Jun 24;465(7301):1027-32. doi: 10.1038/nature09125.
5
Total synthesis of the antiviral peptide antibiotic feglymycin.抗病毒肽抗生素费格霉素的全合成。
Angew Chem Int Ed Engl. 2009;48(10):1856-61. doi: 10.1002/anie.200804130.
6
Amide bond formation: beyond the myth of coupling reagents.酰胺键形成：超越偶联试剂的神话。
Chem Soc Rev. 2009 Feb;38(2):606-31. doi: 10.1039/b701677h. Epub 2008 Dec 4.
7
N-heterocyclic carbene (NHC)-catalyzed direct amidation of aldehydes with nitroso compounds.N-杂环卡宾（NHC）催化醛与亚硝基化合物的直接酰胺化反应。
Org Lett. 2008 Jun 19;10(12):2333-6. doi: 10.1021/ol8004276. Epub 2008 May 14.
8
The antiviral antibiotic feglymycin: first direct-methods solution of a 1000+ equal-atom structure.抗病毒抗生素非格霉素：1000多个等原子结构的首个直接法解决方案。
Angew Chem Int Ed Engl. 2005 Feb 18;44(9):1340-2. doi: 10.1002/anie.200461933.
9
Developments in peptide and amide synthesis.肽与酰胺合成的进展。
Curr Opin Chem Biol. 2004 Jun;8(3):211-21. doi: 10.1016/j.cbpa.2004.03.002.
10
Large-scale manufacture of peptide therapeutics by chemical synthesis.通过化学合成大规模生产肽类治疗药物。
Nat Rev Drug Discov. 2003 Jul;2(7):587-93. doi: 10.1038/nrd1133.
Zotero 插件