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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 18, 1988 - Issue 13
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Original Articles

Synthesis of 3-Hydroxy-2-Methylene Carbonyl Compounds - Effect of Catalyst and Substrate on Reaction Rate

Siegfried E. Drewes Chemistry Department, University of Natal, Pietermaritzburg, South Africa
,
Susan D. Freese Chemistry Department, University of Natal, Pietermaritzburg, South Africa
,
Neville D. Emslie Chemistry Department, University of Natal, Pietermaritzburg, South Africa
&
Gregory H. P. Roos Chemistry Department, University of Natal, Pietermaritzburg, South Africa
Pages 1565-1572 | Published online: 03 Jan 2007

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G. Jenner. (1999) Comparative high pressure and water effect in the Baylis-Hillman reaction. High Pressure Research 16:4, pages 243-252.
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GregoryH. P. Roos & Pradish Rampersadh. (1993) Temperature and Ultrasound Rate Enhancement in the Baylis-Hillman Reaction. Synthetic Communications 23:9, pages 1261-1266.
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Thavrin Manickum & Gregory Roos. (1991) Stereoselective Addition of Methyl Acrylate to α-Amino Aldehydes. Synthetic Communications 21:22, pages 2269-2274.
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Rasmus A. T. Verdier, Jesper H. Mikkelsen & Anders T. Lindhardt. (2018) Studying the Morita-Baylis-Hillman Reaction in Continuous Flow Using Packed Bed Reactors. Organic Process Research & Development 22:11, pages 1524-1533.
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Hong-Yong Kim, Wen-Chung Shieh & Mahavir Prashad. (2014) 3-Quinuclidinol as a nucleophilic catalyst for the cyanation of 2-chloropyrimidines. Tetrahedron Letters 55:36, pages 5055-5057.
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Sanhao Ji, Bernd Bruchmann & Harm‐Anton Klok. (2011) Exploring the Scope of the Baylis–Hillman Reaction for the Synthesis of Side‐Chain Functional Polyesters. Macromolecular Chemistry and Physics 212:24, pages 2612-2618.
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Sanhao Ji, Bernd Bruchmann & Harm-Anton Klok. (2011) Synthesis of Side-Chain Functional Polyesters via Baylis–Hillman Polymerization. Macromolecules 44:13, pages 5218-5226.
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Min Shi, Feijun Wang, Mei-Xin Zhao & Yin WeiMei-Xin Zhao, Yin Wei & Min Shi. 2011. The Chemistry of the Morita-Baylis-Hillman Reaction. The Chemistry of the Morita-Baylis-Hillman Reaction 79 208 .
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Liang Dong, Song Qin, Zhishan Su, Huaqing Yang & Changwei Hu. (2010) Computational investigation on the mechanism and the stereoselectivity of Morita–Baylis–Hillman reaction and the effect of the bifunctional catalyst N-methylprolinol. Organic & Biomolecular Chemistry 8:17, pages 3985.
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Ying Song, Haihua Ke, Nan Wang, Limin Wang & Gang Zou. (2009) Baylis–Hillman reaction promoted by a recyclable protic-ionic-liquid solvent–catalyst system: DABCO–AcOH–H2O. Tetrahedron 65:45, pages 9086-9090.
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Abigail G. Doyle & Eric N. Jacobsen. (2007) Small-Molecule H-Bond Donors in Asymmetric Catalysis. Chemical Reviews 107:12, pages 5713-5743.
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Ciarán Ó Dálaigh & Stephen J. Connon. (2007) Nonenzymatic Acylative Kinetic Resolution of Baylis−Hillman Adducts. The Journal of Organic Chemistry 72:18, pages 7066-7069.
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Cathy Kar‐Wing Kwong, Rui Huang, Minjuan Zhang, Min Shi & Patrick H. Toy. (2007) Bifunctional Polymeric Organocatalysts and Their Application in the Cooperative Catalysis of Morita–Baylis–Hillman Reactions. Chemistry – A European Journal 13:8, pages 2369-2376.
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San-Hu Zhao, Hai-Rong Zhang, Li-Heng Feng & Zhao-Bin Chen. (2006) Pyridinium ionic liquids-accelerated amine-catalyzed Morita–Baylis–Hillman reaction. Journal of Molecular Catalysis A: Chemical 258:1-2, pages 251-256.
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Xueling Mi, Sanzhong Luo, Hui Xu, Long Zhang & Jin-Pei Cheng. (2006) Hydroxyl ionic liquid (HIL)-immobilized quinuclidine for Baylis–Hillman catalysis: synergistic effect of ionic liquids as organocatalyst supports. Tetrahedron 62:11, pages 2537-2544.
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Makoto Ubukata, Kengo Shigetomi, Takao Kishimoto & Kazuaki Shoji. (2006) Synthesis of Tulipalin B and 1-O-Methyl-6-tuliposide B. HETEROCYCLES 69:1, pages 63.
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Min Shi & Wen Zhang. (2005) Organocatalysts of tertiary-phosphines and amines catalyzed reactions of α-keto esters with cyclopent-2-enone. Tetrahedron 61:50, pages 11887-11894.
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Cornelia Faltin, Eimear M. Fleming & Stephen J. Connon. (2004) Acrylamide in the Baylis−Hillman Reaction:  Expanded Reaction Scope and the Unexpected Superiority of DABCO over More Basic Tertiary Amine Catalysts. The Journal of Organic Chemistry 69:19, pages 6496-6499.
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Nolan T. McDougal, Whitney L. Trevellini, Stacy A. Rodgen, Laura T. Kliman & Scott E. Schaus. (2004) The Development of the Asymmetric Morita—Baylis—Hillman Reaction Catalyzed by Chiral Brønsted Acids. Advanced Synthesis & Catalysis 346:9-10, pages 1231-1240.
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Palakodety Radha Krishna, A. Manjuvani, V. Kannan & G.V.M. Sharma. (2004) Sulpholane––A new solvent for the Baylis–Hillman reaction. Tetrahedron Letters 45:6, pages 1183-1185.
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Yujiro Hayashi, Kotaro Okado, Itaru Ashimine & Mitsuru Shoji. (2002) The Baylis–Hillman reaction under high pressure induced by water-freezing. Tetrahedron Letters 43:48, pages 8683-8686.
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Richard S. Grainger, Nicholas E. Leadbeater & Anna Masdéu Pàmies. (2002) The tetramethylguanidine catalyzed Baylis–Hillman reaction: Effects of co-catalysts and alcohol solvents on reaction rate. Catalysis Communications 3:10, pages 449-452.
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Daniela Balan & Hans Adolfsson. (2002) Titanium Isopropoxide as Efficient Catalyst for the Aza-Baylis−Hillman Reaction. Selective Formation of α-Methylene-β-amino Acid Derivatives. The Journal of Organic Chemistry 67:7, pages 2329-2334.
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