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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 22, 1992 - Issue 1
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Original Articles

Malic Acid as a Chiral Synthon: Synthesis of 1,2 and 1,3 Optically Active Diols

Mohamadou Thiam Laboratoire de Chimie Organique Physique, URA CNRS 463, 43 Bd du 11 novembre 1918-69622, Villeurbanne Cedex, France; Université Cheikh Anta Diop, Dakar, Sénégal
,
Abdelmalik Slassi Laboratoire de Chimie Organique Physique, URA CNRS 463, 43 Bd du 11 novembre 1918-69622, Villeurbanne Cedex, France
,
Francine Chastrette Laboratoire de Chimie Organique Physique, URA CNRS 463, 43 Bd du 11 novembre 1918-69622, Villeurbanne Cedex, France
&
Roger Amouroux Laboratoire de Chimie Organique Physique, URA CNRS 463, 43 Bd du 11 novembre 1918-69622, Villeurbanne Cedex, France
Pages 83-95 | Received 04 Jul 1991, Published online: 23 Sep 2006

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A. Kutner, M. Chodyñski & S.J. Halkes. (1996) Citramalic Acid As Chiral Synthon. Synthesis of Chiral Aliphatic Sulfones. Synthetic Communications 26:6, pages 1175-1182.
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J.S. Yadav, K. Vishweshwar Rao, M. Sridhar Reddy & A.R. Prasad. (2006) Stereoselective synthesis of (−)-tetrahydrolipstatin via a radical cyclization based strategy. Tetrahedron Letters 47:26, pages 4393-4395.
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David D. Díaz, Miguel A. Ramírez & Víctor S. Martín. (2006) [1,3]‐Transfer of Chirality during the Nicholas Reaction in γ‐Benzyloxy Propargylic Alcohols. Chemistry – A European Journal 12:9, pages 2593-2606.
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Herbert Frauenrath, Dirk Brethauer, Stefan Reim, Martin Maurer & Gerhard Raabe. (2001) Die hochenantioselektive katalytische Doppelbindungsisomerisierung von 4,7-Dihydro-1,3-dioxepinen mit Me-DuPHOS-modifizierten Dihalogenonickel-Komplexen und Bestimmung der Absolutkonfiguration der Isomerisierungsprodukte. Angewandte Chemie 113:1, pages 176-178.
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Gregory R. Ott & Clayton H. Heathcock. (1999) A Method for Constructing the C44−C51 Side Chain of Altohyrtin C. Organic Letters 1:9, pages 1475-1478.
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Bernhard Wünsch & Sven Nerdinger. (1999) Diastereoselective Addition of Chiral (2-Lithiophenyl)acetaldehyde Acetals to Various Imines as Key Step in the Asymmetric Synthesis of 1-Aryltetrahydroisoquinolines, Part 4. European Journal of Organic Chemistry 1999:2, pages 503-517.
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H. Keith Chenault, Laura F. Chafin & Sebastian Liehr. (1998) Kinetic Chiral Resolutions of 1,2-Diols and Desymmetrization of Glycerol Catalyzed by Glycerol Kinase. The Journal of Organic Chemistry 63:12, pages 4039-4045.
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Dieter Enders & Ulrich Reinhold. (1997) Asymmetric synthesis of amines by nucleophilic 1,2-addition of organometallic reagents to the CN-double bond. Tetrahedron: Asymmetry 8:12, pages 1895-1946.
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Francisco Sánchez-Sancho, Serafín Valverde & Bernardo Herradón. (1996) Stereoselective syntheses and reactions of chiral oxygenated α,β-unsaturated-γ- and δ-lactones. Tetrahedron: Asymmetry 7:11, pages 3209-3246.
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Barbara Achmatowicz, Pawel Jankowski & Jerzy Wicha. (1996) Enantioselective syntheses of a 1α-hydroxyvitamin D ring A precursor from 3-(triphenylsilyl)glycidol and from malic acid. Tetrahedron Letters 37:31, pages 5589-5592.
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Achille Barco, Simonetta Benetti, Carmela De Risi, Gian P Pollini, Giampiero Spalluto & Vinicio Zanirato. (1996) 4-Isopropyl-2-oxazolin-5-one anion as masked umpoled synthon for both formyl and hydroxycarbonyl anions: Generation, reactivity and synthetic applications. Tetrahedron 52:13, pages 4719-4734.
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Masaichi Naruse, Sakae Aoyagi & Chihiro Kibayashi. (1996) Stereoselective total synthesis of (–)-pumiliotoxin C by an aqueous intramolecular acylnitroso Diels–Alder approach. J. Chem. Soc., Perkin Trans. 1:11, pages 1113-1124.
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Chihiro Kibayashi & Sakae Aoyagi. 1996. Structure and Chemistry (Part E). Structure and Chemistry (Part E) 3 88 .
Bernhard Wünsch & Heike Diekmann. (2006) Synthesis of (1 S ,5 S )‐4,5‐Dihydro‐1,5‐epoxy‐1 H ‐2‐benzoxocin‐6(3 H )‐one from ( S )‐Malic Acid Derivatives . Liebigs Annalen 1996:1, pages 69-76.
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Bernhard Wünsch & Sven Nerdinger. (1995) Asymmetric synthesis of 1-aryl-1,2,3,4-tetrahydroisoquinolines part 1: aDDITION of chiral phenylacetaldehyde acetals to acylimines. Tetrahedron Letters 36:44, pages 8003-8006.
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Marcel P.M. van Aar, Lambertus Thijs & Binne Zwanenburg. (1995) Stereoselective synthesis of enantiopure 4,5-dihydroxy-2-alkene esters from simple allylic alcohols. Tetrahedron 51:35, pages 9699-9712.
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Bernhard Wünsch, Heike Diekmann & Georg Höfner. (1995) Stereoselective synthesis of 2-aminoethyl substituted tricycles with NMDA receptor affinity. Tetrahedron: Asymmetry 6:7, pages 1527-1530.
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Masaichi Naruse, Sakae Aoyagi & Chihiro Kibayashi. (1994) Total synthesis of (−)-pumiliotoxin C by aqueous intramolecular acylnitroso Diels-Alder approach. Tetrahedron Letters 35:49, pages 9213-9216.
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Bernardo Herradón & Serafín Valverde. (1994) Biocatalytic synthesis of chiral polyoxygenated compounds: modulation of the selectivity upon changes in the experimental conditions. Tetrahedron: Asymmetry 5:8, pages 1479-1500.
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Masaichi Naruse, Sakae Aoyagi & Chihiro Kibayashi. (1994) Enhanced stereoselectivity in aqueous intramolecular hetero Diels-Alder cycloaddition of chiral acylnitroso compounds. Tetrahedron Letters 35:4, pages 595-598.
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Armin Börner, Jacques Ward, Wolfgang Ruth, Jens Holz, Achim Kless, Detlef Heller & Henri B. Kagan. (1994) Synthesis and catalytic properties of an acyclic analogue of hydroxy norphos. Tetrahedron 50:35, pages 10419-10430.
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Richard Eck & Helmut Simon. (1994) Preparation of both enantiomers of malic and citramalic acid and other hydroxysuccinic acid derivatives by stereospecific hydrations of cis or trans 2-butene-1,4-dioic acids with resting cells of Clostridium formicoaceticum. Tetrahedron 50:48, pages 13641-13654.
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Rudolf O. Duthaler. (1994) Recent developments in the stereoselective synthesis of α-aminoacids. Tetrahedron 50:6, pages 1539-1650.
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Bernhard Wünsch, Heike Diekmann & Georg Höfner. (2006) Homochirale 2,4‐disubstituierte 1,3‐Dioxane aus ( S )‐(−)‐Äpfelsäure: Stereoselektive Synthese und Untersuchung der NMDA‐Rezeptoraffinität aller vier Stereoisomerer . Liebigs Annalen der Chemie 1993:12, pages 1273-1278.
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Bernardo Herradón, Sénida Cueto, Anabel Morcuende & Serafín Valverde. (1993) Regio- and enantioselective esterifications of polyoxygenated compounds catalyzed by lipases. Tetrahedron: Asymmetry 4:5, pages 845-864.
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M. THIAM, A. SLASSI, F. CHASTRETTE & R. AMOUROUX. (2010) ChemInform Abstract: Malic Acid as a Chiral Synthon: Synthesis of 1,2‐ and 1,3‐Optically Active Diols.. ChemInform 23:23.
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