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Pure Appl. Chem., 2005, Vol. 77, No. 12, pp. 1985-1990

http://dx.doi.org/10.1351/pac200577121985

Synthetic methodology using tertiary phosphines as nucleophilic catalysts

Xiyan Lu, Yishu Du and Cheng Lu

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China

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  • Yang Li-Jun, Cai Hua, Nie Jing, Ma Jun-An: A Highly Regio- and Diastereoselective Phosphane-Catalyzed [3+2] Annulation of Morita-Baylis-Hillman Carbonates with Cyclic N -Acyl Ketimines. Eur. J. Org. Chem. 2013, 2013, 4434. <http://dx.doi.org/10.1002/ejoc.201300342>
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  • Zhang Xiao-Nan, Shi Min: Phosphine-Catalyzed [3 + 2] Cycloaddition of 4,4-Dicyano-2-methylenebut-3-enoates with Benzyl Buta-2,3-dienoate and Penta-3,4-dien-2-one. ACS Catal. 2013, 3, 507. <http://dx.doi.org/10.1021/cs300751a>
  • Yu Hao, Zhang Lei, Yang Zhilin, Li Zhen, Zhao Yan, Xiao Yumei, Guo Hongchao: Phosphine-Catalyzed [3 + 2] Cycloaddition of Sulfamate-Derived Cyclic Imines with Allenoate: Synthesis of Sulfamate-Fused Dihydropyrroles. J. Org. Chem. 2013, 78, 8427. <http://dx.doi.org/10.1021/jo401107v>
  • Li Erqing, Huang You, Liang Ling, Xie Peizhong: Phosphine-Catalyzed [4 + 2] Annulation of γ-Substituent Allenoates: Facile Access to Functionalized Spirocyclic Skeletons. Org. Lett. 2013, 15, 3138. <http://dx.doi.org/10.1021/ol401249e>
  • Zheng Jie, Huang You, Li Zhengming: Phosphine-Catalyzed Domino Benzannulation: An Efficient Method to Construct Biaryl Skeletons. Org. Lett. 2013, 15, 5064. <http://dx.doi.org/10.1021/ol4022904>
  • Yang Li-Jun, Wang Shuai, Nie Jing, Li Shen, Ma Jun-An: Bisphosphine-Triggered One-Pot Sequential [3 + 2]/[3 + 2] Annulation of Allenoates with Cyclic Ketimines. Org. Lett. 2013, 15, 5214. <http://dx.doi.org/10.1021/ol402364t>
  • Zheng Jie, Huang You, Li Zhengming: Phosphine-Catalyzed Domino Reaction: An Efficient Method for the Synthesis of Bicyclo[3.2.0]heptenes Skeleton. Org. Lett. 2013, 15, 5758. <http://dx.doi.org/10.1021/ol402799w>
  • Zhang Lei, Yu Hao, Yang Zhilin, Liu Honglei, Li Zhen, Guo Junhong, Xiao Yumei, Guo Hongchao: Phosphine-catalyzed [3 + 2] cycloaddition of Morita–Baylis–Hillman carbonates with sulfamate-derived cyclic imines. Org. Biomol. Chem. 2013, 11, 8235. <http://dx.doi.org/10.1039/c3ob41651h>
  • Jing Chengfeng, Na Risong, Wang Bo, Liu Honglei, Zhang Lei, Liu Jun, Wang Min, Zhong Jiangchun, Kwon Ohyun, Guo Hongchao: Phosphine-Catalyzed [3+2] and [4+3] Annulation Reactions of C,N-Cyclic Azomethine Imines with Allenoates. Synth Catal 2012, 354, 1023. <http://dx.doi.org/10.1002/adsc.201100831>
  • Xie Peizhong, Lai Wenqing, Geng Zhishuai, Huang You, Chen Ruyu: Phosphine-Catalyzed Domino Reaction for the Synthesis of Conjugated 2,3-Dihydrofurans from Allenoates and Nazarov Reagents. Chem. Asian J. 2012, 7, 1533. <http://dx.doi.org/10.1002/asia.201200140>
  • Steurer Marianne, Jensen Kim L., Worgull Dennis, Jørgensen Karl Anker: Enantioselective One-Pot Synthesis of α-Amino Esters by a Phosphine-Catalyzed [3+2]-Cycloaddition Reaction. Chemistry A European Journal 2012, 18, 76. <http://dx.doi.org/10.1002/chem.201103502>
  • Xie Peizhong, Huang You, Chen Ruyu: Phosphine-Mediated Domino Benzannulation Strategy for the Construction of Highly Functionalized Multiaryl Skeletons. Chem. Eur. J. 2012, 18, 7362. <http://dx.doi.org/10.1002/chem.201200305>
  • Sun Lihui, Wang Tong, Ye Song: N-Heterocyclic Carbene-Catalyzed [2+2+2] Annulation of Allenoates with Trifluoromethylketones. Chin J Chem 2012, 30, 190. <http://dx.doi.org/10.1002/cjoc.201100383>
  • Chuang Shih-Ching, Deng Jie-Cheng, Chan Fu-Wei, Chen Sheng-Yuan, Huang Wei-Je, Lai Li-Hsiang, Rajeshkumar Venkatachalam: [3+2] Cycloaddition of Dialkyl (E)-Hex-2-en-4-ynedioates to [60]Fullerene by Phosphane-Promoted Tandem α(δ′)-Michael Additions. Eur J Org 2012, 2012, 2606. <http://dx.doi.org/10.1002/ejoc.201200024>
  • Deng Jie-Cheng, Chan Fu-Wei, Kuo Chih-Wei, Cheng Chun-An, Huang Chien-Yu, Chuang Shih-Ching: Assembly of Dimethyl Acetylenedicarboxylate and Phosphanes with Aldehydes Leading to γ-Lactones Bearing α-Phosphorus Ylides as Wittig Reagents. Eur. J. Org. Chem. 2012, 2012, 5738. <http://dx.doi.org/10.1002/ejoc.201200400>
  • Khong San, Kwon Ohyun: One-Pot Phosphine-Catalyzed Syntheses of Quinolines. J. Org. Chem. 2012, 77, 8257. <http://dx.doi.org/10.1021/jo3015825>
  • Fan Yi Chiao, Kwon Ohyun: Phosphine/Palladium-Catalyzed Syntheses of Alkylidene Phthalans, 3-Deoxyisoochracinic Acid, Isoochracinic Acid, and Isoochracinol. Org. Lett. 2012, 14, 3264. <http://dx.doi.org/10.1021/ol301154f>
  • Hu Jian, Dong Wei, Wu Xin-Yan, Tong Xiaofeng: PPh3-Catalyzed (3 + 3) Annulations of 5-Acetoxypenta-2,3-dienoate with 1C,3O-Bisnucleophiles: Facile Entry to Stable Monocyclic 2H-Pyrans. Org. Lett. 2012, 14, 5530. <http://dx.doi.org/10.1021/ol302634p>
  • Zhang Xiao-nan, Deng Hong-Ping, Huang Long, Wei Yin, Shi Min: Phosphine-catalyzed asymmetric [4+1] annulation of Morita–Baylis–Hillman carbonates with dicyano-2-methylenebut-3-enoates. Chem. Commun. 2012, 48, 8664. <http://dx.doi.org/10.1039/c2cc34619b>
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  • Yang Lihua, Xie Peizhong, Li Erqing, Li Xin, Huang You, Chen Ruyu: Phosphine-catalyzed domino reaction: an efficient method for the synthesis of highly functionalized spirooxazolines. Org. Biomol. Chem. 2012, 10, 7628. <http://dx.doi.org/10.1039/c2ob26338f>
  • Meng Wei, Zhao Hai-Tao, Nie Jing, Zheng Yan, Fu Aiping, Ma Jun-An: Allenoate-derived 1,5-, 1,7-, and 1,9-zwitterions as highly versatile coupling-partners for phosphine-triggered cycloaddition reactions. Chem. Sci. 2012, 3, 3053. <http://dx.doi.org/10.1039/c2sc20805a>
  • Liu Jun, Liu Honglei, Na Risong, Wang Guiyong, Li Zhen, Yu Hao, Wang Min, Zhong Jiangchun, Guo Hongchao: Phosphine-catalyzed [3 + 2] and [3 + 3] Annulations of Azomethine Imines with Ethyl 2-Butynoate. Chem Lett (Japan) 2012, 41, 218. <http://dx.doi.org/10.1246/cl.2012.218>
  • Wang Xiaojun, Fang Tong, Tong Xiaofeng: Enantioselective Amine-Catalyzed [4+2] Annulations of Allenoates and Oxo-dienes: An Asymmetric Synthesis of Dihydropyrans. angew chemie 2011, 123, 5473. <http://dx.doi.org/10.1002/ange.201100945>
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  • Tran Yang S., Martin Tioga J., Kwon Ohyun: Phosphine-Catalyzed [4+2] Annulations of 2-Alkylallenoates and Olefins: Synthesis of Multisubstituted Cyclohexenes. Chem —Asian J 2011, 6, 2101. <http://dx.doi.org/10.1002/asia.201100190>
  • Li Jian, Liu Yuejin, Li Chunju, Jia Xueshun: Syntheses of Spirocyclic Oxindole-Butenolides by Using Three-Component Cycloadditions of Isocyanides, Allenoates, and Isatins. Chem Eur J 2011, 17, 7409. <http://dx.doi.org/10.1002/chem.201100977>
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  • Xie Peizhong, Wang Liye, Yang Lihua, Li Erqing, Ma Jianze,, Huang You, Chen Ruyu: Domino Reaction for the Chemo- and Stereoselective Synthesis of trans-2,3-Dihydrobenzofurans from N-Thiophosphinyl Imines and Sulfur Ylides. J Org Chern 2011, 76, 7699. <http://dx.doi.org/10.1021/jo2008737>
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  • Szeto Judy, Sriramurthy Vardhineedi, Kwon Ohyun: Phosphine-Initiated General Base Catalysis: Facile Access to Benzannulated 1,3-Diheteroatom Five-Membered Rings via Double-Michael Reactions of Allenes. Org Lett 2011, 13, 5420. <http://dx.doi.org/10.1021/ol201730q>
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  • Liu Huimin, Zhang QiongMei, Wang Limin, Tong Xiaofeng: PPh3-Catalyzed Reactions of Alkyl Propiolates with N-Tosylimines: A Facile Synthesis of Alkyl 2-[aryl(tosylimino)methyl]acrylate and an Insight into the Reaction Mechanism. Chem Eur J 2010, 16, 1968. <http://dx.doi.org/10.1002/chem.200902105>
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  • Khong San N., Tran Yang S., Kwon Ohyun: Equilibrium between a vinylogous ylide and a phosphonium dienolate zwitterion: vinylogous Wittig olefination versus vinylogous aldol-type reaction. Tetrahedron 2010, 66, 4760. <http://dx.doi.org/10.1016/j.tet.2010.03.044>
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  • Zhang Qiongmei, Yang Lei, Tong Xiaofeng: 2-(Acetoxymethyl)buta-2,3-dienoate, a Versatile 1,4-Biselectrophile for Phosphine-Catalyzed (4 + n) Annulations with 1,n-Bisnucleophiles (n = 1, 2). J Am Chem Soc 2010, 132, 2550. <http://dx.doi.org/10.1021/ja100432m>
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