研究非环状硝基亚烯与亲核试剂的分子间共轭加成的立体化学。
Investigation of the stereochemistry of intermolecular conjugate additions of nucleophiles to acyclic nitrosoalkenes.
机构信息
Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA.
出版信息
Org Lett. 2011 Mar 4;13(5):1258-60. doi: 10.1021/ol2000793. Epub 2011 Feb 4.
Abstract
Michael-type conjugate additions of γ-chiral aldehyde-derived acyclic nitrosoalkenes have been explored using a series of carbon and hetero nucleophiles. In all cases examined, these reactions are stereoselective, leading exclusively to the anti products.
摘要
使用一系列碳亲核试剂和杂亲核试剂探索了γ-手性醛衍生的无环亚硝酮的迈克尔型共轭加成反应。在所检查的所有情况下，这些反应都是立体选择性的，仅得到反式产物。
相似文献
1
Investigation of the stereochemistry of intermolecular conjugate additions of nucleophiles to acyclic nitrosoalkenes.研究非环状硝基亚烯与亲核试剂的分子间共轭加成的立体化学。
Org Lett. 2011 Mar 4;13(5):1258-60. doi: 10.1021/ol2000793. Epub 2011 Feb 4.
2
Catalytic diastereo- and enantioselective annulations between transient nitrosoalkenes and indoles.过渡态亚硝酮与吲哚的催化非对映选择性和对映选择性环加成反应。
Chemistry. 2012 Dec 21;18(52):16612-5. doi: 10.1002/chem.201203435. Epub 2012 Nov 30.
3
Further studies of intramolecular Michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems.进一步研究亚硝基烯的分子内迈克尔反应，构建功能化桥环体系。
J Org Chem. 2011 Apr 1;76(7):2094-101. doi: 10.1021/jo1024392. Epub 2011 Feb 28.
4
Hetero-Diels-Alder reaction of phosphinyl and phosphonyl nitroso alkenes with conjugated dienes: an aza-Cope rearrangement.膦基和亚膦酰基硝基烯烃与共轭二烯的杂[4+2]环加成反应：氮杂 Cope 重排。
J Org Chem. 2011 Aug 19;76(16):6715-25. doi: 10.1021/jo201116u. Epub 2011 Jul 15.
5
Hetero-Diels-Alder reaction of phosphorylated nitroso alkenes with enol ethers on water: a clean approach toward 1,2-oxazine derivatives.水相中磷酸化亚硝基烯烃与烯醇醚的杂环狄尔斯-阿尔德反应：一种合成1,2-恶嗪衍生物的清洁方法。
J Org Chem. 2014 Aug 15;79(16):7607-15. doi: 10.1021/jo501339c. Epub 2014 Jul 31.
6
Tetrasubstituted olefins through the stereoselective catalytic intermolecular conjugate addition of simple alkenes to α,β-unsaturated carbonyl compounds.通过立体选择性催化的简单烯烃与α,β-不饱和羰基化合物的分子间共轭加成反应合成四取代烯烃。
Angew Chem Int Ed Engl. 2011 Feb 11;50(7):1692-5. doi: 10.1002/anie.201006411. Epub 2011 Jan 14.
7
Direct, enantioselective α-alkylation of aldehydes using simple olefins.使用简单烯烃对醛进行直接、对映选择性 α-烷基化。
Nat Chem. 2017 Nov;9(11):1073-1077. doi: 10.1038/nchem.2797. Epub 2017 Jun 26.
8
Highly efficient asymmetric Michael addition of aldehyde to nitroolefin using perhydroindolic acid as a chiral organocatalyst.手性吲哚烷羧酸高效不对称迈克尔加成醛到硝基烯烃。
Org Biomol Chem. 2012 Apr 14;10(14):2840-6. doi: 10.1039/c2ob00003b. Epub 2012 Mar 2.
9
Recent Advances in Asymmetric Organocatalyzed Conjugate Additions to Nitroalkenes.不对称有机催化向硝基烯烃的共轭加成反应的最新进展
Molecules. 2017 May 29;22(6):895. doi: 10.3390/molecules22060895.
10
Asymmetric Conjugate Addition of α,α-Disubstituted Aldehydes to Nitroalkenes Organocatalyzed by Chiral Monosalicylamides from trans-Cyclohexane-1,2-Diamines.手性单水杨酰胺催化的反式-1,2-环己二胺衍生的亚砜诱导的α,α-二取代醛与硝基烯烃的不对称共轭加成。
Molecules. 2018 Jan 11;23(1):141. doi: 10.3390/molecules23010141.
引用本文的文献
1
Conjugated nitrosoalkenes as Michael acceptors in carbon-carbon bond forming reactions: a review and perspective.共轭亚硝基烯烃作为碳-碳键形成反应中的迈克尔受体：综述与展望
Beilstein J Org Chem. 2017 Oct 23;13:2214-2234. doi: 10.3762/bjoc.13.220. eCollection 2017.
2
Stereochemical investigation of conjugate additions of carbon- and heteronucleophiles to ring-substituted nitrosocyclohexenes.碳亲核试剂和杂亲核试剂对环取代亚硝基环己烯进行共轭加成的立体化学研究。
Tetrahedron. 2011 Oct 28;67(43):8229-8234. doi: 10.1016/j.tet.2011.08.054.
3
Further studies of intramolecular Michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems.进一步研究亚硝基烯的分子内迈克尔反应，构建功能化桥环体系。
J Org Chem. 2011 Apr 1;76(7):2094-101. doi: 10.1021/jo1024392. Epub 2011 Feb 28.
本文引用的文献
1
(S,2S,3S)-2-(2-Methyl-propan-2-sulfin-amido)-3-phenyl-butyronitrile.（S，2S，3S）-2-（2-甲基-丙烷-2-亚磺酰胺基）-3-苯基-丁腈
Acta Crystallogr Sect E Struct Rep Online. 2009 Oct 17;65(Pt 11):o2742. doi: 10.1107/S1600536809041245.
2
Further studies of intramolecular Michael reactions of nitrosoalkenes for construction of functionalized bridged ring systems.进一步研究亚硝基烯的分子内迈克尔反应，构建功能化桥环体系。
J Org Chem. 2011 Apr 1;76(7):2094-101. doi: 10.1021/jo1024392. Epub 2011 Feb 28.
3
Nucleophilic α-arylation and α-alkylation of ketones by polarity inversion of N-alkoxyenamines: entry to the umpolung reaction at the α-carbon position of carbonyl compounds.通过N-烷氧基烯胺的极性翻转实现酮的亲核α-芳基化和α-烷基化：羰基化合物α-碳位置的极性转换反应研究
Angew Chem Int Ed Engl. 2011 Jan 24;50(4):928-31. doi: 10.1002/anie.201004374. Epub 2010 Nov 23.
4
Efficient methodology for alkylation of vinylnitroso compounds with carbon nucleophiles.用碳亲核试剂使乙烯基亚硝基化合物烷基化的有效方法。
Tetrahedron Lett. 2010 Apr 14;51(15):2032-2035. doi: 10.1016/j.tetlet.2010.02.050.
5
Copper(I)-catalyzed addition of Grignard reagents to in situ-derived N-sulfonyl azoalkenes: an umpolung alkylation procedure applicable to the formation of up to three contiguous quaternary centers.铜（I）催化的格氏试剂对原位生成的 N-磺酰基氮杂环丁烯的加成：一种适用于形成多达三个连续季碳原子的极性反转烷基化反应。
J Am Chem Soc. 2010 Apr 7;132(13):4546-7. doi: 10.1021/ja100932q.
6
An efficient preparation of N-methyl-alpha-amino acids from N-nosyl-alpha-amino acid phenacyl esters.从 N-亚硝酰基-α-氨基酸苯乙酰酯制备 N-甲基-α-氨基酸的有效方法。
J Org Chem. 2010 Mar 5;75(5):1386-92. doi: 10.1021/jo901643f.
7
Construction of bridged and fused ring systems via intramolecular Michael reactions of vinylnitroso compounds.通过乙烯基亚硝基化合物的分子内迈克尔反应构建桥环和稠环体系。
J Am Chem Soc. 2007 Aug 29;129(34):10342-3. doi: 10.1021/ja074108r. Epub 2007 Aug 3.
8
Direct and enantioselective organocatalytic alpha-chlorination of aldehydes.醛的直接对映选择性有机催化α-氯化反应
J Am Chem Soc. 2004 Apr 7;126(13):4108-9. doi: 10.1021/ja049562z.
Zotero 插件