通过三氟甲磺酸铟介导的与酰基亚硝基-Diels-Alder加合物的亲核开环反应，实现区域和立体化学控制的异羟肟酸的形成。
Regio- and stereochemically controlled formation of hydroxamic acids from indium triflate-mediated nucleophilic ring-opening reactions with acylnitroso-Diels-Alder adducts.
作者信息
Yang Baiyuan, Miller Marvin J
机构信息
Department of Chemistry and Biochemistry, 251 Nieuwland Science Hall, University of Notre Dame, Notre Dame, IN 46556, United States.
出版信息
Tetrahedron Lett. 2010 Feb 10;51(6):889-891. doi: 10.1016/j.tetlet.2009.12.006.
Abstract
Treatment of acylnitroso-Diels-Alder [2.2.1] bicyclic adducts 2a-b with indium triflate in an alcohol solvent induces ring opening reactions to afford monocyclic anti-1,2-, anti-1,4- and syn-1,4-hydroxamic acids with good to excellent regio- and stereoselectivity (up to 7:86:7). Treatment of [2.2.2] bicyclic nitroso adducts 2c-d under similar reaction conditions generates only anti-1,2- and anti-1,4-hydroxamic acids with anti-1,4-product predominant (up to 17:83).
摘要
在醇溶剂中，用三氟甲磺酸铟处理酰基亚硝基-Diels-Alder [2.2.1] 双环加合物2a-b会引发开环反应，以良好至优异的区域和立体选择性（高达7:86:7）生成单环反式-1,2-、反式-1,4-和顺式-1,4-异羟肟酸。在类似反应条件下处理[2.2.2] 双环亚硝基加合物2c-d，仅生成反式-1,2-和反式-1,4-异羟肟酸，且反式-1,4-产物占主导（高达17:83）。
相似文献
1
Regio- and stereochemically controlled formation of hydroxamic acids from indium triflate-mediated nucleophilic ring-opening reactions with acylnitroso-Diels-Alder adducts.
Tetrahedron Lett. 2010 Feb 10;51(6):889-891. doi: 10.1016/j.tetlet.2009.12.006.
2
Regio- and stereochemically controlled formation of hydroxamic acid containing anti- or syn-1,4-cycloalkenols from acylnitroso-derived Diels-Alder adducts.
J Org Chem. 2001 Apr 6;66(7):2466-9. doi: 10.1021/jo010094a.
3
Regio- and stereoselective indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems.
J Org Chem. 2009 Oct 16;74(20):7990-3. doi: 10.1021/jo9016343.
4
Regio- and stereoselective ring openings of 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene systems with copper catalyst-modified grignard reagents: application to the synthesis of an inhibitor of 5-lipoxygenase.
J Org Chem. 2002 Jun 14;67(12):4115-21. doi: 10.1021/jo016275u.
5
Solid-supported nitroso hetero Diels-Alder reactions. 1. Acylnitroso dienophiles: scope and limitations.
J Comb Chem. 2008 Jan-Feb;10(1):94-103. doi: 10.1021/cc700140h. Epub 2007 Dec 8.
6
Stereo- and regioselectivity of Pd(0)/InI-mediated allylic additions to aldehydes and ketones. In situ generation of allylindium(III) intermediates from N-acylnitroso Diels-Alder cycloadducts and 1-amino-4-acetoxycyclopentenes.
J Org Chem. 2003 Jan 10;68(1):139-49. doi: 10.1021/jo026488z.
7
8
Type 2 intramolecular N-acylnitroso diels-alder reaction: stereoselective synthesis of bridged bicyclic oxazinolactams.
Org Lett. 2002 Aug 8;4(16):2637-40. doi: 10.1021/ol026075k.
9
Oxidative cycloaddition of hydroxamic acids with dienes or guaiacols mediated by iodine(III) reagents.
Beilstein J Org Chem. 2018 Feb 28;14:531-536. doi: 10.3762/bjoc.14.39. eCollection 2018.
10
Rh(I)-catalyzed ring-opening of hetaryne-furan Diels-Alder adducts: rapid access to stereochemically defined heterocyclic scaffolds.
Org Lett. 2011 Mar 18;13(6):1370-3. doi: 10.1021/ol200057j. Epub 2011 Feb 24.
引用本文的文献
1
N-O chemistry for antibiotics: discovery of N-alkyl-N-(pyridin-2-yl)hydroxylamine scaffolds as selective antibacterial agents using nitroso Diels-Alder and ene chemistry.
J Med Chem. 2011 Oct 13;54(19):6843-58. doi: 10.1021/jm200794r. Epub 2011 Sep 15.
2
Cyclopropanation of nitroso Diels-Alder cycloadducts and application to the synthesis of a 2',3'-methano carbocyclic nucleoside.
Tetrahedron Lett. 2010 Jul 1;51(29):3789-3791. doi: 10.1016/j.tetlet.2010.05.062.
本文引用的文献
1
Regio- and stereoselective indium triflate-mediated nucleophilic ring-opening reactions of 3-aza-2-oxabicyclo[2.2.1]hept-5-ene and -[2.2.2]oct-5-ene systems.
J Org Chem. 2009 Oct 16;74(20):7990-3. doi: 10.1021/jo9016343.
2
Rhodium-catalyzed ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with arylboronic acids.
J Org Chem. 2009 Oct 2;74(19):7261-6. doi: 10.1021/jo901248w.
3
Ruthenium-catalyzed nucleophilic ring-opening reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with alcohols.
Org Lett. 2009 May 21;11(10):2077-80. doi: 10.1021/ol900454q.
4
Hydroxyurea and hydroxamic acid derivatives as antitumor drugs.
Cancer Chemother Pharmacol. 2009 Jul;64(2):213-21. doi: 10.1007/s00280-009-0991-z. Epub 2009 Apr 7.
5
Synthesis and anticancer activity of new hydroxamic acid containing 1,4-benzodiazepines.
Org Lett. 2009 Apr 2;11(7):1575-8. doi: 10.1021/ol900210h.
6
Titanocene(III) chloride-mediated reductions of oxazines, hydroxamic acids, and N-hydroxy carbamates.
J Org Chem. 2009 Jan 2;74(1):448-51. doi: 10.1021/jo802184y.
7
Discovery of indium complexes as water-tolerant Lewis acids.
Chem Commun (Camb). 2006 Jul 14(26):2739-49. doi: 10.1039/b600568n.
8
Stereoselective total synthesis of (+)-streptazolin by using a temporary silicon-tethered RCM strategy.
J Org Chem. 2006 Jul 7;71(14):5221-7. doi: 10.1021/jo060555y.
9
The synthesis and in vitro testing of structurally novel antibiotics derived from acylnitroso Diels-Alder adducts.
Bioorg Med Chem Lett. 2006 Aug 1;16(15):3966-70. doi: 10.1016/j.bmcl.2006.05.021. Epub 2006 May 26.
10
3-nitrocoumarins as dienophiles in the Diels-Alder reaction in water. An approach to the synthesis of nitrotetrahydrobenzo[c]chromenones and dihydrodibenzo[b,d]furans.
J Org Chem. 2003 Nov 28;68(24):9263-8. doi: 10.1021/jo034956e.
Zotero 插件