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Journal articles on the topic 'Desymmetrization of anhydride'

Author: Grafiati

Published: 4 June 2021

Last updated: 10 February 2022

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1

Rovis, Tomislav, Brian Cochran, Daniel Henderson, and Scott Thullen. "Rhodium-Catalyzed Desymmetrization of meso-Glutaric Anhydrides to Access Enantioenriched anti,anti-Polypropionates." Synlett 29, no. 03 (2017): 306–9. http://dx.doi.org/10.1055/s-0036-1591488.

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An expedient desymmetrization of 3,5-dimethyl-4-alkoxyglutaric anhydrides to access anti,anti-polypropionates is described. The previously unknown anhydrides are rapidly assembled from readily available precursors. A Rh(I)·t-BuPHOX catalyst system was found to provide good yield and high selectivities. With these conditions, the trisubstituted anhydrides were desymmetrized with various alkyl zinc reagents to provide synthetically useful enantioenriched anti,anti-2,4-dimethyl-3-hydroxy-δ-ketoacids. An identical catalyst system also affords access to syn,syn-stereotriads as well as a partial kin

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2

Valderas, Carolina, Luis Casarrubios, María C. de la Torre, and Miguel A. Sierra. "The organocatalytic desymmetrization of meso-ferrocene anhydride." Tetrahedron Letters 58, no. 4 (2017): 326–28. http://dx.doi.org/10.1016/j.tetlet.2016.12.025.

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3

Wipf, Peter, and Michel Grenon. "Toward the total synthesis of lophotoxin — New methodologies and synthetic strategies." Canadian Journal of Chemistry 84, no. 10 (2006): 1226–41. http://dx.doi.org/10.1139/v06-073.

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Our recent progress toward the synthesis of the furanocembranolide lophotoxin (1) is disclosed. Strategies for the stereoselective incorporation of the C13 stereocenter by a catalytic desymmetrization of a cyclic meso-anhydride, as well as a novel 1,6-addition reaction of organocuprates to unsaturated [1,3]dioxin-4-ones are discussed. Preliminary results on the development of a rhodium-catalyzed asymmetric 1,6-addition reaction are also mentioned. Finally, modifications of a previously reported transition-metal-catalyzed cyclization reaction involving α-propargyl β-keto esters allow furan ring

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4

Shiogai, Akihiro, Tatsuya Toma, and Satoshi Yokoshima. "Synthetic Studies on Bilobalide." Synlett 31, no. 03 (2020): 290–94. http://dx.doi.org/10.1055/s-0039-1691559.

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We disclose our synthetic studies on bilobalide, which features a Diels–Alder reaction of a cyclic anhydride to form two contiguous quaternary carbon centers, desymmetrization of a symmetric diol, and construction of a cyclic acetal under acidic conditions with inversion of configuration at an allylic position.

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5

Rovis, Tomislav, and Matthew Cook. "Enantioselective Rhodium-Catalyzed Alkylative Desymmetrization of 3,5-Dimethylglutaric Anhydride." Synthesis 2009, no. 02 (2008): 335–38. http://dx.doi.org/10.1055/s-0028-1083275.

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6

Frings, Marcus, Isabelle Thomé, and Carsten Bolm. "Synthesis of chiral sulfoximine-based thioureas and their application in asymmetric organocatalysis." Beilstein Journal of Organic Chemistry 8 (September 3, 2012): 1443–51. http://dx.doi.org/10.3762/bjoc.8.164.

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For the first time, chiral sulfoximine derivatives have been applied as asymmetric organocatalysts. In combination with a thiourea-type backbone the sulfonimidoyl moiety leads to organocatalysts showing good reactivity in the catalytic desymmetrization of a cyclic meso-anhydride and moderate enantioselectivity in the catalytic asymmetric Biginelli reaction. Straightforward synthetic routes provide the newly designed thiourea-sulfoximine catalysts in high overall yields without affecting the stereohomogeneity of the sulfur-containing core fragment.

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7

Ivšić, Trpimir, and Zdenko Hameršak. "A simple enantioselective route toward (R)- and (S)-Rolipram via anhydride desymmetrization." Tetrahedron: Asymmetry 24, no. 4 (2013): 217–22. http://dx.doi.org/10.1016/j.tetasy.2013.01.009.

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8

Yamada, Ken-ichi, Akinori Oonishi, Yusuke Kuroda, et al. "Desymmetrization of acid anhydride with asymmetric esterification catalyzed by chiral phosphoric acid." Tetrahedron Letters 57, no. 36 (2016): 4098–100. http://dx.doi.org/10.1016/j.tetlet.2016.07.093.

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9

Boussonnière, Anne, Anne-Sophie Castanet, and Hélène Guyon. "Transition-Metal-Free Enantioselective Reactions of Organomagnesium Reagents Mediated by Chiral Ligands." Synthesis 50, no. 18 (2018): 3589–602. http://dx.doi.org/10.1055/s-0037-1610135.

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Organomagnesium reagents are among the most important reagents in organic chemistry because of their great utility in forming carbon–carbon bonds. Although most enantioselective reactions using these organometallics involve transmetalation, the past decade has witnessed impressive advances in direct chiral-ligand-mediated reactions of organomagnesiums. This short review presents an overview of these achievements in enantioselective nucleophilic additions and substitutions.1 Introduction2 Enantioselective Nucleophilic Additions2.1 Addition to C=O Bonds2.2 Addition to C=N Bonds2.3 Addition to C

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10

Liu, Weiming, Yi Hu, Yang Zhang, Yan Ma, and He Huang. "Enzymatic desymmetrization of 3-(4-fluorophenyl)glutaric anhydride through enantioselective alcoholysis in organic solvents." Biotechnology and Bioprocess Engineering 19, no. 3 (2014): 449–55. http://dx.doi.org/10.1007/s12257-014-0110-9.

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11

Real, Sharon D., David R. Kronenthal, and Helen Y. Wu. "A novel and highly efficient desymmetrization of a meso-anhydride by a chiral grignard reagent." Tetrahedron Letters 34, no. 50 (1993): 8063–66. http://dx.doi.org/10.1016/s0040-4039(00)61451-x.

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12

Peschiulli, Aldo, Barbara Procuranti, Cornelius J. O' Connor, and Stephen J. Connon. "Synergistic organocatalysis in the kinetic resolution of secondary thiols with concomitant desymmetrization of an anhydride." Nature Chemistry 2, no. 5 (2010): 380–84. http://dx.doi.org/10.1038/nchem.584.

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13

Cook, Matthew J., and Tomislav Rovis. "Rhodium-Catalyzed Enantioselective Desymmetrization ofmeso-3,5-Dimethyl Glutaric Anhydride: A General Strategy tosyn-Deoxypolypropionate Synthons." Journal of the American Chemical Society 129, no. 30 (2007): 9302–3. http://dx.doi.org/10.1021/ja073269s.

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14

Díaz de Villegas, María D., José A. Gálvez, Pablo Etayo, Ramón Badorrey, and Pilar López-Ram-de-Víu. "Recent advances in enantioselective organocatalyzed anhydride desymmetrization and its application to the synthesis of valuable enantiopure compounds." Chemical Society Reviews 40, no. 11 (2011): 5564. http://dx.doi.org/10.1039/c1cs15120g.

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15

REAL, S. D., D. R. KRONENTHAL, and H. Y. WU. "ChemInform Abstract: A Novel and Highly Efficient Desymmetrization of a meso-Anhydride by a Chiral Grignard Reagent." ChemInform 25, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199413159.

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16

Hameršak, Zdenko, Irena Stipetić, and Amir Avdagić. "An efficient synthesis of (S)-3-aminomethyl-5-methylhexanoic acid (Pregabalin) via quinine-mediated desymmetrization of cyclic anhydride." Tetrahedron: Asymmetry 18, no. 12 (2007): 1481–85. http://dx.doi.org/10.1016/j.tetasy.2007.06.014.

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17

Blise, Katie, Milan W. Cvitkovic, Nolly J. Gibbs, et al. "A Theoretical Mechanistic Study of the Asymmetric Desymmetrization of a Cyclic meso-Anhydride by a Bifunctional Quinine Sulfonamide Organocatalyst." Journal of Organic Chemistry 82, no. 3 (2017): 1347–55. http://dx.doi.org/10.1021/acs.joc.6b02320.

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18

Diaz de Villegas, Maria D., Jose A. Galvez, Pablo Etayo, Ramon Badorrey, and Pilar Lope-Ram-de-Viu. "ChemInform Abstract: Recent Advances in Enantioselective Organocatalyzed Anhydride Desymmetrization and Its Application to the Synthesis of Valuable Enantiopure Compounds." ChemInform 43, no. 6 (2012): no. http://dx.doi.org/10.1002/chin.201206235.

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19

Verma, Rekha, and Sunil K. Ghosh. "Desymmetrization of 3-dimethyl(phenyl)silyl glutaric anhydride with Evans’ oxazolidinone: an application to stereocontrolled synthesis of the antifungal agent (+)-preussin." Journal of the Chemical Society, Perkin Transactions 1, no. 3 (1999): 265–70. http://dx.doi.org/10.1039/a808840c.

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20

Chen, Xiaofei, Fangjun Xiong, Wenxue Chen, Qiuqin He, and Fener Chen. "Asymmetric Synthesis of the HMG-CoA Reductase Inhibitor Atorvastatin Calcium: An Organocatalytic Anhydride Desymmetrization and Cyanide-Free Side Chain Elongation Approach." Journal of Organic Chemistry 79, no. 6 (2014): 2723–28. http://dx.doi.org/10.1021/jo402829b.

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21

Xiong, Fei, Xu-Xiang Chen, and Fen-Er Chen. "An improved asymmetric total synthesis of (+)-biotin via the enantioselective desymmetrization of a meso-cyclic anhydride mediated by cinchona alkaloid-based sulfonamide." Tetrahedron: Asymmetry 21, no. 6 (2010): 665–69. http://dx.doi.org/10.1016/j.tetasy.2010.03.041.

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22

Verma, Rekha, and Sunil K. Ghosh. "ChemInform Abstract: Desymmetrization of 3-Dimethyl(phenyl)silyl Glutaric Anhydride with Evans′ Oxazolidinone: An Application to Stereocontrolled Synthesis of the Antifungal Agent (+)-Preussin." ChemInform 30, no. 24 (2010): no. http://dx.doi.org/10.1002/chin.199924220.

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23

Chen, Xiaofei, Fangjun Xiong, Wenxue Chen, Qiuqin He, and Fener Chen. "ChemInform Abstract: Asymmetric Synthesis of the HMG-CoA Reductase Inhibitor Atorvastatin Calcium: An Organocatalytic Anhydride Desymmetrization and Cyanide-Free Side Chain Elongation Approach." ChemInform 45, no. 36 (2014): no. http://dx.doi.org/10.1002/chin.201436221.

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24

Chaubey, Narendra R., and Sunil K. Ghosh. "An enantiodivergent and formal synthesis of paroxetine enantiomers by asymmetric desymmetrization of 3-(4-fluorophenyl)glutaric anhydride with a chiral SuperQuat oxazolidin-2-one." Tetrahedron: Asymmetry 23, no. 15-16 (2012): 1206–12. http://dx.doi.org/10.1016/j.tetasy.2012.08.001.

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25

Takata, Shohei, Yuta Endo, Mohammad Shahid Ullah, and Shinichi Itsuno. "Synthesis of cinchona alkaloid sulfonamide polymers as sustainable catalysts for the enantioselective desymmetrization of cyclic anhydrides." RSC Advances 6, no. 76 (2016): 72300–72305. http://dx.doi.org/10.1039/c6ra14535c.

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Mizoroki–Heck polymerization of cinchona sulfonamide gave chiral polymers, which are active catalysts for enantioselective desymmetrization of cyclic anhydrides to give chiral hemiesters in high yield with high enantioselectivities.

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26

Ostaszewski, R., D. E. Portlock, Anna Fryszkowska, and Katarzyna Jeziorska. "Combination of enzymatic procedures with multicomponent condensations." Pure and Applied Chemistry 75, no. 2-3 (2003): 413–19. http://dx.doi.org/10.1351/pac200375020413.

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A new synthetic method based on combination of enzymatic desymmetrization of 3-phenylglutaric anhydrides with multicomponent condensation is outlined. Enzymatic monoesterification of glutaric anhydrides was performed, and the derived monoacids were used as substrates for subsequent Ugi and Passerini multicomponent condensations. Both reactions were combined as two-step, one-pot processes. The choice of solvent and enzyme type has an appreciable effect on the course of reactions.

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27

Song, C., S. Park, E. Nam, et al. "Highly Efficient Desymmetrization of Glutaric Anhydrides." Synfacts 2010, no. 12 (2010): 1423. http://dx.doi.org/10.1055/s-0030-1258921.

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28

Schmitt, Ellen, Ingo Schiffers, and Carsten Bolm. "Highly enantioselective desymmetrizations of meso-anhydrides." Tetrahedron 66, no. 33 (2010): 6349–57. http://dx.doi.org/10.1016/j.tet.2010.04.121.

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29

Fryszkowska, Anna, Marta Komar, Dominik Koszelewski, and Ryszard Ostaszewski. "Enzymatic desymmetrization of 3-arylglutaric acid anhydrides." Tetrahedron: Asymmetry 16, no. 14 (2005): 2475–85. http://dx.doi.org/10.1016/j.tetasy.2005.06.025.

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30

Hashimoto, Kimiko, Jun-ichi Kitaguchi, Yasuhiro Mizuno, Tadao Kobayashi та Haruhisa Shirahama. "A new reagent for the preparation of chiral HMGA (3-hydroxy-3-methylglutaric acid) esters and amides. Synthesis of (R)- and (S)-β-carboxymethyl-β-methyl-β-lactones by asymmetric desymmetrization of HMGA anhydride". Tetrahedron Letters 37, № 13 (1996): 2275–78. http://dx.doi.org/10.1016/0040-4039(96)00274-2.

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31

HASHIMOTO, K., J. KITAGUCHI, Y. MIZUNO, T. KOBAYASHI та H. SHIRAHAMA. "ChemInform Abstract: A New Reagent for the Preparation of Chiral HMGA (3-Hydroxy-3- methylglutaric Acid) Esters and Amides. Synthesis of (R)- and (S)-. beta.-Carboxymethyl-β-methyl-β-lactones by Asymmetric Desymmetrization of HMGA Anhydride." ChemInform 27, № 28 (2010): no. http://dx.doi.org/10.1002/chin.199628101.

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32

Rovis, Tomislav, Kevin Oberg, Brian Cochran, and Matthew Cook. "The Catalytic Alkylative Desymmetrization of Anhydrides in a Formal Synthesis of Ionomycin." Synthesis 50, no. 22 (2018): 4343–50. http://dx.doi.org/10.1055/s-0037-1610108.

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The catalytic desymmetrization of anhydrides with zinc reagents provides access to deoxypolypropionate and polypropionate synthons. A synthesis of ionomycin was pursued in which three of the four fragments were assembled using this methodology. Two of the strategies (enol silane/oxocarbenium coupling and reductive cyclization) were not successful at installing the C23 stereocenter, but this stereochemical issue was overcome through a reduction/SN2 approach. In addition to the synthesis of a protected diastereomer of ionomycin, the synthesis of a C17–C32 fragment constitutes a formal total synt

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33

Schmitt, Ellen, Ingo Schiffers, and Carsten Bolm. "ChemInform Abstract: Highly Enantioselective Desymmetrizations of meso-Anhydrides." ChemInform 42, no. 1 (2010): no. http://dx.doi.org/10.1002/chin.201101021.

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34

Bercot, Eric A., and Tomislav Rovis. "A Palladium-Catalyzed Enantioselective Alkylative Desymmetrization ofmeso-Succinic Anhydrides." Journal of the American Chemical Society 126, no. 33 (2004): 10248–49. http://dx.doi.org/10.1021/ja046528b.

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35

Batovska, Daniela I., Shuichirou Tsubota, Yasuo Kato, Yasuhisa Asano, and Makoto Ubukata. "Lipase-mediated desymmetrization of glycerol with aromatic and aliphatic anhydrides." Tetrahedron: Asymmetry 15, no. 22 (2004): 3551–59. http://dx.doi.org/10.1016/j.tetasy.2004.09.033.

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36

ALBERS, T., S. C. G. BIAGINI, D. E. HIBBS, et al. "ChemInform Abstract: Desymmetrization of meso-Anhydrides Utilizing (S)-Proline Derivatives." ChemInform 27, no. 33 (2010): no. http://dx.doi.org/10.1002/chin.199633096.

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37

JONES, I. G., W. JONES, M. NORTH, M. TEIJEIRA, and E. URIARTE. "ChemInform Abstract: Desymmetrization of Bicyclic, meso-Anhydrides by Proline Esters." ChemInform 28, no. 23 (2010): no. http://dx.doi.org/10.1002/chin.199723225.

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38

Ivšić, Trpimir, and Zdenko Hameršak. "Inversion of enantioselectivity in quinine-mediated desymmetrization of glutaric meso-anhydrides." Tetrahedron: Asymmetry 20, no. 10 (2009): 1095–98. http://dx.doi.org/10.1016/j.tetasy.2009.02.049.

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39

Stache, Erin E., Tomislav Rovis, and Abigail G. Doyle. "Dual Nickel- and Photoredox-Catalyzed Enantioselective Desymmetrization of Cyclic meso -Anhydrides." Angewandte Chemie International Edition 56, no. 13 (2017): 3679–83. http://dx.doi.org/10.1002/anie.201700097.

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40

Stache, Erin E., Tomislav Rovis, and Abigail G. Doyle. "Dual Nickel- and Photoredox-Catalyzed Enantioselective Desymmetrization of Cyclic meso -Anhydrides." Angewandte Chemie 129, no. 13 (2017): 3733–37. http://dx.doi.org/10.1002/ange.201700097.

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41

Liu, Tang-Lin, Wei Li, Huiling Geng, Chun-Jiang Wang, and Xumu Zhang. "Catalytic Enantioselective Desymmetrization of Meso Cyclic Anhydrides via Iridium-Catalyzed Hydrogenation." Organic Letters 15, no. 7 (2013): 1740–43. http://dx.doi.org/10.1021/ol400533g.

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42

Liu, Tang-Lin, Wei Li, Huiling Geng, Chun-Jiang Wang, and Xumu Zhang. "Catalytic Enantioselective Desymmetrization of Meso Cyclic Anhydrides via Iridium-Catalyzed Hydrogenation." Organic Letters 15, no. 8 (2013): 2072. http://dx.doi.org/10.1021/ol400886w.

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43

Chen, Yonggang, Shi-Kai Tian, and Li Deng. "A Highly Enantioselective Catalytic Desymmetrization of Cyclic Anhydrides with Modified Cinchona Alkaloids." Journal of the American Chemical Society 122, no. 39 (2000): 9542–43. http://dx.doi.org/10.1021/ja001765+.

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44

Muthusamy, Sengodagounder, Boopathy Gnanaprakasam, and Eringathodi Suresh. "Desymmetrization of Cyclic Anhydrides Using Dihydroxy Compounds: Selective Synthesis of Macrocyclic Tetralactones." Organic Letters 8, no. 9 (2006): 1913–16. http://dx.doi.org/10.1021/ol060509k.

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45

Dedeoglu, Burcu, Saron Catak, Asli Yildirim, Carsten Bolm, and Viktorya Aviyente. "Cinchona Alkaloid Catalyzed Asymmetric Desymmetrization ofmeso-Cyclic Anhydrides: The Origins of Stereoselectivity." ChemCatChem 7, no. 24 (2015): 4173–79. http://dx.doi.org/10.1002/cctc.201500852.

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46

Martin, Anthony, Frédéric Robert, Daniel Taton, Henri Cramail, Jean-Marc Vincent, and Yannick Landais. "Organocatalyzed Step-Growth Polymerization through Desymmetrization of Cyclic Anhydrides: Synthesis of Chiral Polyesters." Chemistry - A European Journal 20, no. 37 (2014): 11946–53. http://dx.doi.org/10.1002/chem.201402373.

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47

Rho, Ho Sik, Sang Ho Oh, Ji Woong Lee, Jin Yong Lee, Jik Chin, and Choong Eui Song. "Bifunctional organocatalyst for methanolytic desymmetrization of cyclic anhydrides: increasing enantioselectivity by catalyst dilution." Chemical Communications, no. 10 (2008): 1208. http://dx.doi.org/10.1039/b719811f.

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48

Chen, Yan ming, Mamatha Amireddy, and Kwunmin Chen. "Organocatalytic desymmetrization of cyclic meso-anhydrides through enantioselective alcoholysis with functionalized primary nitroallylic alcohols." Tetrahedron 70, no. 47 (2014): 9064–69. http://dx.doi.org/10.1016/j.tet.2014.10.008.

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49

Uozumi, Yasuhiro, Kayo Yasoshima, Takamasa Miyachi, and Shin-ichi Nagai. "Enantioselective desymmetrization of meso-cyclic anhydrides catalyzed by hexahydro-1H-pyrrolo[1,2-c]imidazolones." Tetrahedron Letters 42, no. 3 (2001): 411–14. http://dx.doi.org/10.1016/s0040-4039(00)01972-9.

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50

Chaubey, Narendra, Sonali M. Date, and Sunil K. Ghosh. "An efficient asymmetric desymmetrization of prochiral glutaric anhydrides with SuperQuat chiral oxazolidin-2-ones." Tetrahedron: Asymmetry 19, no. 23 (2008): 2721–30. http://dx.doi.org/10.1016/j.tetasy.2008.12.010.

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