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However, the synthetic utility of DHF\u2019s nucleophilic reactivity, contained in the ene\u2013diol moiety, has been underexplored. Inspired by recently observed pH-dependent chemodivergent nucleophilic aldol reactions of dihydroxyfumarate (DHF2\u2013) with glyoxylate and formaldehyde, we report herein the control and synthetic application of base-controlled chemodivergent reactions between dihydroxyfumarate and aromatic and heteroaromatic aldehydes. With hydroxide as the base in a predominantly aqueous medium, aldol addition followed by deoxalation occurs to provide various 3-aryl-2,3-dihydroxypropanoic acids. With triethylamine as the base in THF, 1-aryl-2,3-dihydroxypropanones are the products of the reaction. In order to understand the difference in reactivity between DHF, its dicarboxylate, and its dimethyl ester, we undertook computational and experimental studies that provide a rationale as to why the dihydroxyfumarate (DHF2\u2013) is a nucleophile while the corresponding diester reacts as an electrophile.<\/jats:p>","DOI":"10.1021\/acs.joc.8b01867","type":"journal-article","created":{"date-parts":[[2018,9,17]],"date-time":"2018-09-17T21:09:22Z","timestamp":1537218562000},"page":"14219-14233","source":"Crossref","is-referenced-by-count":9,"title":["Base-Mediated Cascade\nAldol Addition and Fragmentation\nReactions of Dihydroxyfumaric Acid and Aromatic Aldehydes: Controlling\nChemodivergence via Choice of Base, Solvent, and Substituents"],"prefix":"10.1021","volume":"83","author":[{"given":"George","family":"Ward","sequence":"first","affiliation":[{"name":"Georgia Institute of Technology , , , ,","place":["Atlanta, Georgia, United States, 30332"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Charles L.","family":"Liotta","sequence":"additional","affiliation":[{"name":"Georgia Institute of Technology , , , ,","place":["Atlanta, Georgia, United States, 30332"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5238-610X","authenticated-orcid":true,"given":"Ramanarayanan","family":"Krishnamurthy","sequence":"additional","affiliation":[{"name":"The Scripps Research Institute , , , ,","place":["La Jolla, California, United States, 92037"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5998-6167","authenticated-orcid":true,"given":"Stefan","family":"France","sequence":"additional","affiliation":[{"name":"Georgia Institute of Technology , , , ,","place":["Atlanta, Georgia, United States, 30332"]},{"name":"Georgia Institute of Technology , , , ,","place":["Atlanta, Georgia, United States, 30332"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2018,9,17]]},"reference":[{"key":"2026090305512570600_cit1a","doi-asserted-by":"publisher","first-page":"774","DOI":"10.1039\/CT8956700774","article-title":"New\nFormation of Glycollic Aldehyde","volume":"67","author":"Fenton","year":"1895","journal-title":"J. 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Mold."},{"key":"2026090305512570600_cit3","doi-asserted-by":"publisher","first-page":"4921","DOI":"10.1021\/jp800208s","article-title":"Kinetic\nStudy of the Hexacyanoferrate\n(III) Oxidation of Dhydroxyfumaric Acid in Acid Media","volume":"112","author":"Garcia","year":"2008","journal-title":"J. Phys. Chem. A"},{"key":"2026090305512570600_cit4","doi-asserted-by":"crossref","first-page":"83","DOI":"10.19261\/cjm.2010.05(2).11","article-title":"Stopped-Flow\nSpectrophotometric Studies of the Kinetics of Interaction of Dihydroxyfumaric\nAcid with the DPPH Free Radical","volume":"5","author":"Secara","year":"2010","journal-title":"Chem. J. Mold."},{"key":"2026090305512570600_cit5","doi-asserted-by":"publisher","first-page":"925","DOI":"10.1007\/s00217-007-0615-y","article-title":"The Production\nof Yellow Pigments from (+)-Catechin and Dihydroxyfumaric Acid in\na Model Wine System","volume":"226","author":"Clark","year":"2008","journal-title":"Eur. Food Res. Technol."},{"key":"2026090305512570600_cit6a","doi-asserted-by":"publisher","first-page":"2","DOI":"10.1016\/j.molstruc.2006.02.009","article-title":"Coordination\nNetworks\nIncorporating the In Situ Generated Ligands [OC(CO2)3]4- and [OCH(CO2)2]3-","volume":"796","author":"Abrahams","year":"2006","journal-title":"J. Mol.\nStruct."},{"key":"2026090305512570600_cit6b","doi-asserted-by":"publisher","first-page":"7095","DOI":"10.1002\/chem.200600323","article-title":"In Situ Synthesis of Trisubstituted\nMethanol Ligands and Their Potential as One-Pot Generators of Cubane-Like\nMetal Complexes","volume":"12","author":"Abrahams","year":"2006","journal-title":"Chem. - Eur. 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See\nthe Supporting Information for calculation\nof cost per milligram."},{"key":"2026090305512570600_cit37","unstructured":"Bicyclic Pyrimidinones and Uses Thereof. WO2008\/77188 A1, 2008, 24\u201325."},{"key":"2026090305512570600_cit38","doi-asserted-by":"publisher","first-page":"613","DOI":"10.1016\/S0040-4020(01)01176-0","article-title":"The Asymmetric Synthesis of \u03b2-aryl-\u03b1-hydroxy\nEsters From\n\u03b2-Aryl-\u03b1,\u03b2-dihyroxy Esters","volume":"58","author":"Lawrence","year":"2002","journal-title":"Tetrahedron"},{"key":"2026090305512570600_cit39","doi-asserted-by":"publisher","first-page":"13349","DOI":"10.1002\/chem.201101978","article-title":"Synthesis of Chondramide A Anoglogues\nwith Modified \u03b2-Tyrosine and Their Biological Evaluation","volume":"17","author":"Zhdanko","year":"2011","journal-title":"Chem. - Eur. 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Chim.\nActa"},{"key":"2026090305512570600_cit43","doi-asserted-by":"publisher","first-page":"11673","DOI":"10.1021\/jf1033398","article-title":"Maple Syrup\nPhytochemicals Include Lignans, Coumarins,\nA Stilbene, and Other Previously Unreported Antioxidant Phenolic Compounds","volume":"58","author":"Li","year":"2010","journal-title":"J. Agric. 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