膦催化的亲核试剂对活化的α-烷基丙二烯的β'-Umpolung 加成反应。
Phosphine-catalyzed β'-umpolung addition of nucleophiles to activated α-alkyl allenes.
机构信息
Department of Chemistry and Biochemistry, University of California, Los Angeles, Los Angeles, California 90095-1569, United States.
出版信息
Org Lett. 2011 May 20;13(10):2586-9. doi: 10.1021/ol200697m. Epub 2011 Apr 14.
Abstract
Highly functionalized alkenes can be prepared through phosphine-catalyzed β'-umpolung additions of nucleophiles (carbon-, oxygen-, nitrogen-, and sulfur-centered) to activated α-disubstituted allenes, providing many potentially useful synthetic intermediates in good to excellent yields, often with high levels of stereoselectivity for the product olefin geometry. Various substitution patterns around the allene are compatible with the process, showcasing the synthetic utility of allenes under the conditions of nucleophilic phosphine catalysis.
摘要
高功能化的烯烃可以通过膦催化的亲核试剂（碳、氧、氮和硫中心）对活化的α-二取代烯丙基的β'-反转加成来制备，以良好至优异的收率提供许多潜在有用的合成中间体，通常产物烯烃几何形状的立体选择性很高。烯丙基周围的各种取代模式与该过程兼容，展示了在亲核膦催化条件下烯丙基的合成实用性。
相似文献
1
Phosphine-catalyzed β'-umpolung addition of nucleophiles to activated α-alkyl allenes.膦催化的亲核试剂对活化的α-烷基丙二烯的β'-Umpolung 加成反应。
Org Lett. 2011 May 20;13(10):2586-9. doi: 10.1021/ol200697m. Epub 2011 Apr 14.
2
Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.亲核膦催化烯烃、丙二烯、炔烃和 MBHADs 的进展。
Chem Commun (Camb). 2013 Dec 25;49(99):11588-619. doi: 10.1039/c3cc47368f.
3
Phosphine-catalyzed [4+2] annulations of 2-alkylallenoates and olefins: synthesis of multisubstituted cyclohexenes.膦催化的 2-烷基金烯酸酯和烯烃的[4+2]环加成反应：多取代环己烯的合成。
Chem Asian J. 2011 Aug 1;6(8):2101-6. doi: 10.1002/asia.201100190. Epub 2011 Jul 7.
4
Phosphine-catalyzed enantioselective intramolecular [3+2] annulations to generate fused ring systems.磷化氢催化的对映选择性分子内[3+2]环化反应以生成稠环体系。
J Am Chem Soc. 2015 Apr 8;137(13):4587-91. doi: 10.1021/jacs.5b01985. Epub 2015 Mar 27.
5
Phosphine-Mediated Iterative Arene Homologation Using Allenes.利用联烯的磷化氢介导的迭代芳烃同系化反应
J Am Chem Soc. 2015 Sep 9;137(35):11258-61. doi: 10.1021/jacs.5b07403. Epub 2015 Aug 31.
6
Phosphine Organocatalysis.膦有机催化。
Chem Rev. 2018 Oct 24;118(20):10049-10293. doi: 10.1021/acs.chemrev.8b00081. Epub 2018 Sep 27.
7
Phosphine catalysis of allenes with electrophiles.亲电试剂对丙二烯的膦催化作用。
Chem Soc Rev. 2014 May 7;43(9):2927-40. doi: 10.1039/c4cs00054d. Epub 2014 Mar 24.
8
Phosphine-initiated general base catalysis: facile access to benzannulated 1,3-diheteroatom five-membered rings via double-Michael reactions of allenes.膦引发的广义碱催化：通过丙二烯的双重迈克尔加成反应，轻松构建苯并稠合的 1,3-双杂原子五元环。
Org Lett. 2011 Oct 21;13(20):5420-3. doi: 10.1021/ol201730q. Epub 2011 Sep 20.
9
Enantioselective Synthesis of Spirobarbiturate-Cyclohexenes through Phosphine-Catalyzed Asymmetric [4 + 2] Annulation of Barbiturate-Derived Alkenes with Allenoates.通过膦催化的巴比特酸盐衍生烯烃与丙二烯酸酯的不对称[4+2]环加成反应，对映选择性合成螺巴比妥酸-环己烯。
Org Lett. 2016 Mar 18;18(6):1302-5. doi: 10.1021/acs.orglett.6b00239. Epub 2016 Mar 3.
10
Phosphine-catalyzed formation of carbon-sulfur bonds: catalytic asymmetric synthesis of gamma-thioesters.膦催化碳-硫键形成反应：γ-硫代酯的催化不对称合成。
J Am Chem Soc. 2010 Apr 7;132(13):4568-9. doi: 10.1021/ja101251d.
引用本文的文献
1
Synthesis of 3,4-Disubstituted Maleimide Derivatives via Phosphine-Catalyzed Isomerization of α-Succinimide-Substituted Allenoates Cascade γ'-Addition with Aryl Imines.通过膦催化的α-琥珀酰亚胺取代的丙二烯酸酯的异构化的 3,4-二取代马来酰亚胺衍生物的合成-芳基亚胺的γ'-加成级联反应。
Int J Mol Sci. 2024 Jun 24;25(13):6916. doi: 10.3390/ijms25136916.
2
Quick construction of a C-N bond from arylsulfonyl hydrazides and C-X compounds promoted by DMAP at room temperature.在室温下，由4-二甲氨基吡啶（DMAP）促进，芳基磺酰肼与碳-卤化合物快速构建碳-氮键。
RSC Adv. 2019 Jun 26;9(35):19917-19923. doi: 10.1039/c9ra03403j. eCollection 2019 Jun 25.
3
Phosphine-Catalyzed (4+1) Annulation: Rearrangement of Allenylic Carbamates to 3-Pyrrolines through Phosphonium Diene Intermediates.膦催化的(4+1)环化反应：通过鏻二烯中间体将烯丙基氨基甲酸酯重排为3-吡咯啉。
ChemCatChem. 2020 Sep 4;12(17):4352-4372. doi: 10.1002/cctc.202000626. Epub 2020 May 22.
4
Phosphine Organocatalysis.膦有机催化。
Chem Rev. 2018 Oct 24;118(20):10049-10293. doi: 10.1021/acs.chemrev.8b00081. Epub 2018 Sep 27.
5
Reaction of allene esters with Selectfluor/TMSX (X = I, Br, Cl) and Selectfluor/NH4SCN: Competing oxidative/electrophilic dihalogenation and nucleophilic/conjugate addition.丙二烯酯与Selectfluor/TMSX（X = I、Br、Cl）及Selectfluor/NH4SCN的反应：竞争性氧化/亲电二卤化及亲核/共轭加成
Beilstein J Org Chem. 2015 Sep 16;11:1641-8. doi: 10.3762/bjoc.11.180. eCollection 2015.
6
Stereoselective Syntheses of α,β-Unsaturated γ-Amino Esters Through Phosphine-Catalyzed γ-Umpolung Additions of Sulfonamides to γ-Substituted Allenoates.通过膦催化磺酰胺对γ-取代联烯酸酯的γ-极性翻转加成反应立体选择性合成α,β-不饱和γ-氨基酯
Tetrahedron Lett. 2015 Jun 3;56(23):3273-3276. doi: 10.1016/j.tetlet.2015.01.120.
7
Advances in nucleophilic phosphine catalysis of alkenes, allenes, alkynes, and MBHADs.亲核膦催化烯烃、丙二烯、炔烃和 MBHADs 的进展。
Chem Commun (Camb). 2013 Dec 25;49(99):11588-619. doi: 10.1039/c3cc47368f.
8
Phosphine-catalyzed intramolecular γ-umpolung addition of α-aminoalkylallenic esters: facile synthesis of 3-carbethoxy-2-alkyl-3-pyrrolines.膦催化的α-氨基烷基烯丙基酯的分子内γ-反转加成：3-乙氧羰基-2-烷基-3-吡咯啉的简便合成。
Chem Commun (Camb). 2012 May 28;48(43):5373-5. doi: 10.1039/c2cc31347b. Epub 2012 Apr 23.
9
Phosphine-initiated general base catalysis: facile access to benzannulated 1,3-diheteroatom five-membered rings via double-Michael reactions of allenes.膦引发的广义碱催化：通过丙二烯的双重迈克尔加成反应，轻松构建苯并稠合的 1,3-双杂原子五元环。
Org Lett. 2011 Oct 21;13(20):5420-3. doi: 10.1021/ol201730q. Epub 2011 Sep 20.
10
Diversity-oriented synthesis based on the DPPP-catalyzed mixed double-Michael reactions of electron-deficient acetylenes and β-amino alcohols.基于 DPPP 催化的缺电子炔烃和β-氨基醇的混合双迈克尔反应的导向多样性合成。
Molecules. 2011 May 5;16(5):3802-25. doi: 10.3390/molecules16053802.
本文引用的文献
1
Equilibrium between a vinylogous ylide and a phosphonium dienolate zwitterion: vinylogous Wittig olefination versus vinylogous aldol-type reaction.乙烯型叶立德与鏻二烯醇盐两性离子之间的平衡：乙烯型维蒂希烯烃化反应与乙烯型羟醛缩合型反应
Tetrahedron. 2010 Jun;66(26):4760-4768. doi: 10.1016/j.tet.2010.03.044.
2
Phosphine-catalyzed tandem reaction of allenoates with nitroalkenes.膦催化的丙二烯酸酯与硝基烯烃的串联反应。
Org Lett. 2010 Nov 5;12(21):5024-7. doi: 10.1021/ol102191p.
3
Diastereoselective synthesis of 6-trifluoromethyl-5,6-dihydropyrans via phosphine-catalyzed [4 + 2] annulation of α-benzylallenoates with ketones.通过膦催化的α-苄基烯丙酸盐与酮的[4 + 2]环加成反应，立体选择性合成 6-三氟甲基-5,6-二氢吡喃。
Org Lett. 2010 Sep 17;12(18):4168-71. doi: 10.1021/ol101762z.
4
Carbon-carbon bond formation and pyrrole synthesis via the [3,3] sigmatropic rearrangement of O-vinyl oxime ethers.通过 O-乙烯基肟醚的[3,3]σ重排反应形成碳-碳键和吡咯合成。
Org Lett. 2010 May 21;12(10):2290-3. doi: 10.1021/ol100659q.
5
PHOSPHINE-CATALYZED [4+2] ANNULATION: SYNTHESIS OF ETHYL 6-PHENYL-1-TOSYL-1,2,5,6-TETRAHYDROPYRIDINE-3-CARBOXYLATE.膦催化的[4+2]环化反应：6-苯基-1-对甲苯磺酰基-1,2,5,6-四氢吡啶-3-羧酸乙酯的合成
Organic Synth. 2009 Mar 1;2009(86):212-224. doi: 10.1002/0471264229.os086.21.
6
2-(Acetoxymethyl)buta-2,3-dienoate, a versatile 1,4-biselectrophile for phosphine-catalyzed (4 + n) annulations with 1,n-Bisnucleophiles (n = 1, 2).2-(乙酰氧基甲基)丁-2,3-二烯酸酯，一种多功能的 1,4-双亲电试剂，用于膦催化的 1,n-双亲核试剂（n = 1, 2）的（4 + n）环加成反应。
J Am Chem Soc. 2010 Mar 3;132(8):2550-1. doi: 10.1021/ja100432m.
7
Enantioselective catalysis and complexity generation from allenoates.手性催化与丙二烯酸酯的复杂度生成。
Chem Soc Rev. 2009 Nov;38(11):3102-16. doi: 10.1039/b816700c. Epub 2009 Jul 24.
8
Asymmetric carbon-carbon bond formation gamma to a carbonyl group: phosphine-catalyzed addition of nitromethane to allenes.羰基γ位的不对称碳-碳键形成：膦催化硝基甲烷与丙二烯的加成反应。
J Am Chem Soc. 2009 Oct 14;131(40):14231-3. doi: 10.1021/ja9061823.
9
Phosphine-promoted [3 + 3] annulations of aziridines with allenoates: facile entry into highly functionalized tetrahydropyridines.磷化氢促进氮丙啶与联烯酸酯的[3 + 3]环化反应：便捷合成高度官能化的四氢吡啶
J Am Chem Soc. 2009 May 13;131(18):6318-9. doi: 10.1021/ja8097349.
10
Phosphine-catalyzed enantioselective synthesis of oxygen heterocycles.膦催化的氧杂环的对映选择性合成。
Angew Chem Int Ed Engl. 2009;48(12):2225-7. doi: 10.1002/anie.200805377.
Zotero 插件