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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 28, 1998 - Issue 14
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Original Articles

Regio- and Diastereoselectivity in the Thiomethylation of α-(1-Hydroxyalkyl)acrylate Derivatives

Philip O. Deane Department of Chemistry, Rhodes University, P O Box 94, Grahamstown, 6140, Republic of South Africa
,
Jeffry J. Guthrie-Strachan Department of Chemistry, Rhodes University, P O Box 94, Grahamstown, 6140, Republic of South Africa
,
Perry T. Kaye Department of Chemistry, Rhodes University, P O Box 94, Grahamstown, 6140, Republic of South Africa
&
Ruth E. Whittaker Department of Chemistry, Rhodes University, P O Box 94, Grahamstown, 6140, Republic of South Africa
Pages 2601-2611 | Received 26 Nov 1997, Published online: 20 Aug 2006

Citations (21)

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Read on this site (2)

Yosra Oueslati, Ahlem Abidi, Hassen Mohamed Sbihi & Farhat Rezgui. (2017) A direct synthetic route to allyl sulfides from cyclic Morita–Baylis–Hillman alcohols. Journal of Sulfur Chemistry 38:2, pages 142-151.
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Debnath Bhuniya, Srinivas Gujjary & Sujata Sengupta. (2006) Synthesis of Novel Oxime Functionalized Aldol Products via Michael Addition of Oximes Onto Baylis–Hillman Adducts. Synthetic Communications 36:2, pages 151-164.
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Articles from other publishers (19)

Rakesh Puttreddy, Anssi Peuronen, Manu Lahtinen & Kari Rissanen. (2019) Metal-Bound Nitrate Anion as an Acceptor for Halogen Bonds in Mono-Halopyridine-Copper(II) Nitrate Complexes. Crystal Growth & Design 19:7, pages 3815-3824.
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Rakhee Choudhary, Rekha Bai, Pratibha Singh, Mahesh C. Sharma & Satpal Singh Badsara. (2017) Metal-free, regio- and stereoselective S-methylation/phenylation of allyl halides using sulfoxides as sulfenylating agent. Tetrahedron 73:30, pages 4323-4328.
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Pratibha Singh, Rekha Bai, Rakhee Choudhary, Mahesh C. Sharma & Satpal Singh Badsara. (2017) Regio- and stereoselective syntheses of allylic thioethers under metal free conditions. RSC Advances 7:49, pages 30594-30602.
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Misael Ferreira & Marcus M. Sá. (2015) Formal [3+2] Annulation Involving Allylic Bromides and Thioureas. Synthesis of 2‐Iminothiazolidines through a Base‐Catalyzed Intramolecular anti ‐Michael Addition . Advanced Synthesis & Catalysis 357:4, pages 829-833.
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Mattia Cocco, Davide Garella, Antonella Di Stilo, Emily Borretto, Livio Stevanato, Marta Giorgis, Elisabetta Marini, Roberto Fantozzi, Gianluca Miglio & Massimo Bertinaria. (2014) Electrophilic Warhead-Based Design of Compounds Preventing NLRP3 Inflammasome-Dependent Pyroptosis. Journal of Medicinal Chemistry 57:24, pages 10366-10382.
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Marcus M. Sá, Misael Ferreira, Giovanni F. Caramori, Laize Zaramello, Adailton J. Bortoluzzi, Deonildo FaggionJr.Jr. & Josiel B. Domingos. (2013) Investigating the Ritter Type Reaction of α-Methylene-β-hydroxy Esters in Acidic Medium: Evidence for the Intermediacy of an Allylic Cation. European Journal of Organic Chemistry 2013:23, pages 5180-5187.
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Koosam Mahendar, A. V. S. Sarma, P. Raghavaiah, Mannepalli Lakshmi Kantam & Kenneth J. Klabunde. (2011) Synthesis of β ‐Hydroxy α ‐Sulfanyl Esters by Using Nanocrystalline Magnesium Oxide . Helvetica Chimica Acta 94:8, pages 1533-1542.
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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 209 324 .
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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Eun-Gu Han, Hea Jung Kim & Kee-Jung Lee. (2009) Quinolines from Morita–Baylis–Hillman acetates of 2-azidobenzaldehydes. Tetrahedron 65:46, pages 9616-9625.
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Lal Dhar S Yadav, Rajesh Patel & Vishnu P. Srivastava. (2009) An easy access to functionalized allyl dithiocarbamates from Baylis–Hillman adducts in water. Tetrahedron Letters 50:12, pages 1335-1339.
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Yunkui Liu, Danqian Xu, Zhenyuan Xu & Yongmin Zhang. (2008) Stereoselective synthesis of trisubstituted alkenes containing (Z)-allylthio units from the acetates of Baylis–Hillman adducts. Heteroatom Chemistry 19:2, pages 188-198.
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Marcus M. Sá, Luciano Fernandes, Misael Ferreira & Adailton J. Bortoluzzi. (2008) Synthesis of allylic thiocyanates and novel 1,3-thiazin-4-ones from 2-(bromomethyl)alkenoates and S-nucleophiles in aqueous medium. Tetrahedron Letters 49:7, pages 1228-1232.
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Akio Kamimura, Rie Morita, Kenji Matsuura, Hiromasa Mitsudera & Masashi Shirai. (2003) A convenient stereoselective synthesis of β-lactams from β-hydroxy-α-thioalkylesters prepared from Michael/aldol tandem reaction or stereoselective addition of thiols to the Baylis–Hillman adducts. Tetrahedron 59:50, pages 9931-9938.
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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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Akio Kamimura, Rie Morita, Kenji Matsuura, Yoji Omata & Masashi Shirai. (2002) Simple preparation of β-hydroxy-α-thiomethyl carbonyl compounds via stereoselective conjugate addition of thiol to Baylis–Hillman adducts. Tetrahedron Letters 43:35, pages 6189-6191.
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Drury Caine. (2001) Reactions of conjugated haloenoates with nucleophilic reagents. Tetrahedron 57:14, pages 2643-2684.
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Magdalini Matziari, Dimitris Georgiadis, Vincent Dive & Athanasios Yiotakis. (2001) Convenient Synthesis and Diversification of Dehydroalaninyl Phosphinic Peptide Analogues. Organic Letters 3:5, pages 659-662.
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P. O. DEANE, J. J. GUTHRIE-STRACHAN, P. T. KAYE & R. E. WHITTAKER. (2010) ChemInform Abstract: Regio- and Diastereoselectivity in the Thiomethylation of α-(1-Hydroxyalkyl)acrylate Derivatives.. ChemInform 29:42, pages no-no.
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