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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 23, 1993 - Issue 20
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Original Articles

Intramolecular Baylis-Hillman Reaction: A Pathway to Substituted Coumarins

Siegfried E. Drewes Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa
,
Owen L. Njamela Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa
,
Neville D. Emslie Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa
,
Niyum Ramesar Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa
&
John S. Field Department of Chemistry, University of Natal, P O Box 375, Pietermaritzburg, 3200, South Africa
Pages 2807-2815 | Received 18 May 1993, Published online: 23 Sep 2006

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S. Satyanarayana Reddy & G. L. David Krupadanam. (2010) Facile Synthesis of 9-Acetyl/Formyl/Cyano-Substituted Pyrano[2,3-f]flavones and Chromones Using the Baylis–Hillman Reaction. Synthetic Communications 40:9, pages 1292-1304.
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Perry T. Kaye & Musiliyu A. Musa. (2004) Regioselectivity of Reactions of Nitrogen and Carbon Nucleophiles with Coumarin Derivatives. Synthetic Communications 34:18, pages 3409-3417.
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Perry T. Kaye, Musiliyu A. Musa, Aloysius T. Nchinda & Xolani W. Nocanda. (2004) Novel Heterocyclic Analogues of the HIV‐1 Protease Inhibitor, Ritonavir. Synthetic Communications 34:14, pages 2575-2589.
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Perry T. Kaye & M. A. Musa. (2003) Application of Baylis–Hillman Methodology in the Synthesis of Coumarin Derivatives. Synthetic Communications 33:10, pages 1755-1770.
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Han-Xun Wei, Steven Willis & Guigen Li. (1999) Z/E Selective Synthesis of β,β-Disubstituted and (Z)-β-Monosubstituted Baylis-Hillman Adducts Via Anionic Additions of Vinylcuprates to Aldehydes. Synthetic Communications 29:17, pages 2959-2966.
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PerryT. Kaye & RossS. Robinson. (1996) Dabco-Catalysed Reactions of Salicylaldehydes with Acrylate Derivatives. Synthetic Communications 26:11, pages 2085-2097.
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S.E. Drewes, R.B. Taylor, N.S. Ramesar & J.S. Field. (1995) Metal-Mediated Reactions of α-Bromomethyl-Propenoate Esters. Synthetic Communications 25:3, pages 321-329.
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Articles from other publishers (52)

Perry T. Kaye. 2019. 101 152 .
Abdol R. Hajipour & Saedeh Zakery. (2018) α ‐ZrP/Uracil/Cu 2+ nanoparticles as an efficient catalyst in the Morita‐Baylis‐Hillman reaction . Applied Organometallic Chemistry 32:10.
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Min Shi, Yin Wei, Mei-Xin Zhao & Jun ZhangYin Wei & Min Shi. 2018. Organocatalytic Cycloadditions for Synthesis of Carbo‐ and Heterocycles. Organocatalytic Cycloadditions for Synthesis of Carbo‐ and Heterocycles 141 236 .
Zhen Liu, Chandan Patel, Jeremy N. Harvey & Raghavan B. Sunoj. (2017) Mechanism and reactivity in the Morita–Baylis–Hillman reaction: the challenge of accurate computations. Physical Chemistry Chemical Physics 19:45, pages 30647-30657.
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Kishor Chandra Bharadwaj. (2015) Intramolecular Morita–Baylis–Hillman and Rauhut–Currier reactions. A catalytic and atom economic route for carbocycles and heterocycles. RSC Advances 5:93, pages 75923-75946.
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Yun Xuan Tan, Sridhar Santhanakrishnan, Hai Yan Yang, Christina L. L. Chai & Eric Kwok Wai Tam. (2014) Synthesis of Neplanocin A and Its 3′-Epimer via an Intramolecular Baylis–Hillman Reaction. The Journal of Organic Chemistry 79:17, pages 8059-8066.
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Mehdi Ghandi, Shahzad Feizi, Farhood Ziaie & Behrouz Notash. (2014) Solvent-dependent Baylis–Hillman reactions for the synthesis of 3-benzyl-3-hydroxyoxindoles and benzo-δ-sultams. Tetrahedron 70:15, pages 2563-2569.
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Yin Wei & Min Shi. 2013. Comprehensive Enantioselective Organocatalysis. Comprehensive Enantioselective Organocatalysis 899 939 .
Yin Wei & Min Shi. (2013) Recent Advances in Organocatalytic Asymmetric Morita–Baylis–Hillman/aza-Morita–Baylis–Hillman Reactions. Chemical Reviews 113:8, pages 6659-6690.
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Mehdi Ghandi, Abolfazl Hasani Bozcheloei, Seyed Hadi Nazari & Masoud Sadeghzadeh. (2011) Solvent-Dependent Reactions for the Synthesis of β-Keto-Benzo-δ-Sultone Scaffolds via DBU-Catalyzed O-Sulfonylation/Intramolecular Baylis–Hillman/1,3-H Shift or Dehydration Tandem Sequences. The Journal of Organic Chemistry 76:24, pages 9975-9982.
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John W. Cran, Marie E. Krafft, Kimberly A. Seibert, Thomas F.N. Haxell, James A. Wright, Chitaru Hirosawa & Khalil A. Abboud. (2011) The intramolecular Morita–Baylis–Hillman-type alkylation reaction. Tetrahedron 67:51, pages 9922-9943.
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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 1 78 .
David Cantillo & C. Oliver Kappe. (2010) A Unified Mechanistic View on the Morita−Baylis−Hillman Reaction: Computational and Experimental Investigations. The Journal of Organic Chemistry 75:24, pages 8615-8626.
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Zerong Wang. 2010. Comprehensive Organic Name Reactions and Reagents. Comprehensive Organic Name Reactions and Reagents 275 283 .
Deevi Basavaiah, Bhavanam Sekhara Reddy & Satpal Singh Badsara. (2010) Recent Contributions from the Baylis−Hillman Reaction to Organic Chemistry. Chemical Reviews 110:9, pages 5447-5674.
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Kristen N. Clary, Masood Parvez & Thomas G. Back. (2010) Rearrangements and Intramolecular Diels−Alder Reactions of Normal and Vinylogous Aza-Morita−Baylis−Hillman Products Leading to Isoindoline Derivatives. The Journal of Organic Chemistry 75:11, pages 3751-3760.
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Mahiuddin Baidya, Grygoriy Y. Remennikov, Peter Mayer & Herbert Mayr. (2010) S N 2’ versus S N 2 Reactivity: Control of Regioselectivity in Conversions of Baylis–Hillman Adducts . Chemistry – A European Journal 16:4, pages 1365-1371.
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Indubhusan Deb, Pramod Shanbhag, Shaikh M. Mobin & Irishi N. N. Namboothiri. (2009) Morita–Baylis–Hillman Reactions Between Conjugated Nitroalkenes or Nitrodienes and Carbonyl Compounds. European Journal of Organic Chemistry 2009:24, pages 4091-4101.
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Sonia Khamri & Hassen Amri. (2009) DABCO-mediated substitution of vinylic iodides: synthesis of β-cyano Baylis–Hillman acetates. Tetrahedron 65:25, pages 4890-4893.
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Sang‐Hyun Ahn, Hee Nam Lim & Kee‐Jung Lee. (2009) Application of the acetate of baylis‐hillman adducts of salicylaldehydes in the synthesis of methyl 2‐oxo‐2,3‐dihydrobenzo[ b ]oxepine‐4‐carboxylates . Journal of Heterocyclic Chemistry 45:6, pages 1701-1706.
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Jun‐Li GAO, Yong‐Kang LIU & Song XUE. (2008) Self‐condensation of Terminal Acetylenic Ketones via Organozinc Species. Chinese Journal of Chemistry 26:9, pages 1689-1692.
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Xiaofang Tang, Bo Zhang, Zhengrong He, Ruili Gao & Zhengjie He. (2007) 1,3,5‐Triaza‐7‐phosphaadamantane (PTA): A Practical and Versatile Nucleophilic Phosphine Organocatalyst. Advanced Synthesis & Catalysis 349:11-12, pages 2007-2017.
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Géraldine Masson, Christopher Housseman & Jieping Zhu. (2007) The Enantioselective Morita–Baylis–Hillman Reaction and Its Aza Counterpart. Angewandte Chemie International Edition 46:25, pages 4614-4628.
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Géraldine Masson, Christopher Housseman & Jieping Zhu. (2007) Enantioselektive Morita‐Baylis‐Hillman‐Reaktionen und ihre Aza‐Varianten. Angewandte Chemie 119:25, pages 4698-4712.
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Leonardo Silva Santos, Brenno A. DaSilveira Neto, Crestina S. Consorti, Cesar Henrique Pavam, Wanda P. Almeida, Fernando Coelho, Jairton Dupont & Marcos N. Eberlin. (2006) The role of ionic liquids in co‐catalysis of Baylis‐Hillman reaction: interception of supramolecular species via electrospray ionization mass spectrometry. Journal of Physical Organic Chemistry 19:11, pages 731-736.
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Jianhua Xu. (2006) Probing the mechanism of Morita–Baylis–Hillman reaction in dichloromethane by density functional theory. Journal of Molecular Structure: THEOCHEM 767:1-3, pages 61-66.
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Yuji Matsuya, Kousuke Hayashi & Hideo Nemoto. (2005) A New Protocol for the Consecutive α‐ and β‐Activation of Propiolates towards Electrophiles, Involving Conjugate Addition of Tertiary Amines and Intramolecular Silyl Migration. Chemistry – A European Journal 11:18, pages 5408-5418.
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Marie E. Krafft & Thomas F. N. Haxell. (2005) Organomediated Morita−Baylis−Hillman Cyclization Reactions. Journal of the American Chemical Society 127:29, pages 10168-10169.
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Marie E. Krafft, Kimberly A. Seibert, Thomas F. N. Haxell & Chitaru Hirosawa. (2005) Unprecedented reactivity in the Morita–Baylis–Hillman reaction; intramolecular α-alkylation of enones using saturated alkyl halides. Chemical Communications:46, pages 5772.
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Palakodety Radha Krishna, V. Kannan & G. V. M. Sharma. (2004) First Diastereoselective Intramolecular Baylis−Hillman Reaction:  An Easy Access to Chiral α-Methylene-β-hydroxylactones. The Journal of Organic Chemistry 69:19, pages 6467-6469.
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Han‐Xun Wei, Jiali Hu, Richard L. Jasoni, Guigen Li & Paul W. Paré. (2004) Synthesis of Substituted α ‐(Hydroxymethyl)‐ β ‐iodoacrylates via MgI 2 ‐Promoted Stereoselective Aldol Coupling . Helvetica Chimica Acta 87:9, pages 2359-2363.
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Leonardo Silva Santos, Cesar Henrique Pavam, Wanda P. Almeida, Fernando Coelho & Marcos N. Eberlin. (2004) Probing the Mechanism of the Baylis–Hillman Reaction by Electrospray Ionization Mass and Tandem Mass Spectrometry. Angewandte Chemie International Edition 43:33, pages 4330-4333.
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Leonardo Silva Santos, Cesar Henrique Pavam, Wanda P. Almeida, Fernando Coelho & Marcos N. Eberlin. (2004) Probing the Mechanism of the Baylis–Hillman Reaction by Electrospray Ionization Mass and Tandem Mass Spectrometry. Angewandte Chemie 116:33, pages 4430-4433.
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Jung Eun Yeo, Xiuling Yang, Hee Jin Kim & Sangho Koo. (2004) The intramolecular Baylis–Hillman reaction: easy preparation of versatile substrates, facile reactions, and synthetic applications. Chem. Commun.:2, pages 236-237.
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Guang‐Hui Deng, Hui Hu, Han‐Xun Wei & Paul W. Paré. (2003) The Aldol Reaction of Allenolates with Aldehydes in the Presence of Magnesium Diiodide (MgI 2 ) as Catalyst . Helvetica Chimica Acta 86:10, pages 3510-3515.
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Deevi Basavaiah, Anumolu Jaganmohan Rao & Tummanapalli Satyanarayana. (2003) Recent Advances in the Baylis−Hillman Reaction and Applications. Chemical Reviews 103:3, pages 811-892.
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Yuji Matsuya, Kousuke Hayashi & Hideo Nemoto. (2002) A Novel Modified Baylis−Hillman Reaction of Propiolate. Journal of the American Chemical Society 125:3, pages 646-647.
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Gary E. Keck & Dennie S. Welch. (2002) Intramolecular Baylis−Hillman and Morita Reactions Using Unsaturated Thiol Ester Substrates Containing Enolizable Aldehydes. Organic Letters 4:21, pages 3687-3690.
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Han-Xun Wei, Guigen Li, Joe J. Gao & Paul W. Paré. (2002) Synthesis of β-iodo-α-(hydroxyalkyl)acrylates: a convenient and stereoselective reaction. Tetrahedron Letters 43:32, pages 5677-5680.
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Scott A. Frank, Dustin J. Mergott & William R. Roush. (2002) The Vinylogous Intramolecular Morita−Baylis−Hillman Reaction:  Synthesis of Functionalized Cyclopentenes and Cyclohexenes with Trialkylphosphines as Nucleophilic Catalysts. Journal of the American Chemical Society 124:11, pages 2404-2405.
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Natalia N. Sergeeva, Alexander S. Golubev, Lothar Hennig, Matthias Findeisen, Eckhard Paetzold, Günther Oehme & Klaus Burger. (2001) An improved approach to trifluoromethyl substituted Morita–Baylis–Hillman adduct: Fluorinated dehydro-β-amino acids. Journal of Fluorine Chemistry 111:1, pages 41-44.
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Wenge Li, Zhaoguo Zhang, Dengming Xiao & Xumu Zhang. (2000) Synthesis of Chiral Hydroxyl Phospholanes from d -mannitol and Their Use in Asymmetric Catalytic Reactions . The Journal of Organic Chemistry 65:11, pages 3489-3496.
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Matthias Rehwald, Peter Bellmann, Torsten Jeschke & Karl Gewald. (2000) Synthese von Hetaryl-pyridiniumsalzen und kondensierten 3-Amino-pyrid-2-onen. Journal für praktische Chemie 342:4, pages 371-378.
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Taı̈cir Ben Ayed, Jean Villiéras & Hassen Amri. (2000) A Stereoselective Synthesis of α-(1-Hydroxyalkyl)-β-Substituted Acrylic Acid Esters. Tetrahedron 56:5, pages 805-809.
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Guigen Li, Han-Xun Wei & Steven Willis. (1998) A new stereospecific synthesis of unusual (Z)-β-branched Baylis-Hillman adducts. Tetrahedron Letters 39:26, pages 4607-4610.
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Gregory P. Black, Francesca Dinon, Silvia Fratucello, Patrick J. Murphy, Michael Nielsen, Harri Lloyd Williams & Nigel D.A. Walshe. (1997) An intramolecular Baylis-Hillman reaction catalysed by secondary amines. Tetrahedron Letters 38:49, pages 8561-8564.
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István E. Marko, Paul R. Giles & Nigel J. Hindley. (1997) Catalytic enantioselective Baylis-Hillman reactions. Correlation between pressure and enantiomeric excess. Tetrahedron 53:3, pages 1015-1024.
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Deevi Basavaiah, Polisetti Dharma Rao & Rachakonda Suguna Hyma. (1996) The Baylis-Hillman reaction: A novel carbon-carbon bond forming reaction. Tetrahedron 52:24, pages 8001-8062.
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S. E. DREWES, O. L. NJAMELA, N. D. EMSLIE, N. RAMESAR & J. S. FIELD. (2010) ChemInform Abstract: Intramolecular Baylis‐Hillman Reaction: A Pathway to Substituted Coumarins.. ChemInform 25:16.
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