亚胺基亚硝基烯反应：关于反应活性、区域选择性和对映选择性的实验研究。
Iminonitroso ene reactions: experimental studies on reactivity, regioselectivity and enantioselectivity.
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 Jan 13;51(2):328-331. doi: 10.1016/j.tetlet.2009.11.015.
Abstract
Ene reactions of iminonitroso agents with olefins were investigated in both solution and solid phase. Reactions afforded allyl hydroxylamine products in up to 99% yield and with high regioselectivity. A Cu(I)-mediated enantioselective nitroso ene reaction gave an ene product with up to 40% ee.
摘要
研究了亚胺基亚硝基试剂与烯烃在溶液和固相中的烯反应。反应得到的烯丙基羟胺产物产率高达99%，且具有高区域选择性。铜（I）介导的对映选择性亚硝基烯反应得到的烯产物对映体过量值（ee）高达40%。
相似文献
1
Iminonitroso ene reactions: experimental studies on reactivity, regioselectivity and enantioselectivity.
Tetrahedron Lett. 2010 Jan 13;51(2):328-331. doi: 10.1016/j.tetlet.2009.11.015.
2
Retro iminonitroso Diels-Alder reactions: interconversion of nitroso cycloadducts.
Tetrahedron Lett. 2009 Oct 1;50(43):5879-5883. doi: 10.1016/j.tetlet.2009.07.121.
3
B(C F ) /Chiral Phosphoric Acid Catalyzed Ketimine-Ene Reaction of 2-Aryl-3H-indol-3-ones and α-Methylstyrenes.
Angew Chem Int Ed Engl. 2020 Mar 9;59(11):4550-4556. doi: 10.1002/anie.201915226. Epub 2020 Jan 29.
4
The mechanism and regioselectivity of the ene reactions of nitroso compounds: a theoretical study of reactivity, regioselectivity, and kinetic isotope effects establishes a stepwise path involving polarized diradical intermediates.
Org Biomol Chem. 2003 Apr 21;1(8):1389-403. doi: 10.1039/b300285c.
5
Organocatalytic Enantioselective Conia-Ene-Type Carbocyclization of Ynamide Cyclohexanones: Regiodivergent Synthesis of Morphans and Normorphans.
Angew Chem Int Ed Engl. 2019 Nov 4;58(45):16252-16259. doi: 10.1002/anie.201908495. Epub 2019 Sep 18.
6
Catalytic Enantioselective Nitroso Diels-Alder Reaction.
J Am Chem Soc. 2015 Dec 23;137(50):15957-63. doi: 10.1021/jacs.5b11273. Epub 2015 Dec 11.
7
Chiral Lewis acid-catalyzed enantioselective intramolecular carbonyl ene reactions of unsaturated alpha-keto esters.
Org Lett. 2003 Oct 2;5(20):3749-52. doi: 10.1021/ol035486d.
8
Catalytic and enantioselective aza-ene and hetero-Diels-Alder reactions of alkenes and dienes with azodicarboxylates.
Org Biomol Chem. 2005 Jun 21;3(12):2344-9. doi: 10.1039/b503744a. Epub 2005 May 19.
9
Bulky monodentate phosphoramidites in palladium-catalyzed allylic alkylation reactions: aspects of regioselectivity and enantioselectivity.
Chemistry. 2004 Dec 3;10(24):6232-46. doi: 10.1002/chem.200400154.
10
Enantioselective transformation of allyl carbonates into branched allyl carbamates by using amines and recycling CO2 under iridium catalysis.
Chemistry. 2014 Jun 10;20(24):7216-21. doi: 10.1002/chem.201402388. Epub 2014 May 18.
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.
本文引用的文献
1
Syntheses and biological activity studies of novel sterol analogs from nitroso Diels-Alder reactions of ergosterol.
Org Lett. 2009 Jul 2;11(13):2828-31. doi: 10.1021/ol900997t.
2
The remarkable cis effect in the ene reactions of nitrosocarbonyl intermediates.
J Org Chem. 2009 Mar 20;74(6):2301-10. doi: 10.1021/jo801641j.
3
Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso Diels-Alder reactions.
Org Lett. 2009 Jan 15;11(2):449-52. doi: 10.1021/ol802553g.
4
Solid-supported nitroso hetero diels-alder reactions. 2. Arylnitroso dienophiles: scope and limitations.
J Comb Chem. 2008 Jan-Feb;10(1):104-11. doi: 10.1021/cc7001414. Epub 2007 Dec 7.
5
Divergent reactions for racemates: catalytic, enantioselective, and regiodivergent nitroso diels-alder reactions.
Angew Chem Int Ed Engl. 2007;46(34):6542-4. doi: 10.1002/anie.200701631.
6
Iminonitroso Diels-Alder reactions for efficient derivatization and functionalization of complex diene-containing natural products.
Org Lett. 2007 Jul 19;9(15):2923-6. doi: 10.1021/ol071322b. Epub 2007 Jun 30.
7
Variable Markovnikov orientation and "cis effect" in ene reactions of nitrosocarbonyl intermediates.
J Org Chem. 2007 Mar 2;72(5):1807-10. doi: 10.1021/jo0622025. Epub 2007 Feb 2.
8
Catalytic asymmetric nitroso-Diels-Alder reaction with acyclic dienes.
Angew Chem Int Ed Engl. 2005 Nov 4;44(43):7082-5. doi: 10.1002/anie.200501345.
9
Rich chemistry of nitroso compounds.
Chem Commun (Camb). 2005 Jul 28(28):3514-25. doi: 10.1039/b503212c. Epub 2005 Jun 24.
10
Catalytic, highly enantio, and diastereoselective nitroso diels-alder reaction.
J Am Chem Soc. 2004 Apr 7;126(13):4128-9. doi: 10.1021/ja049849w.
Zotero 插件