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Artículos de revistas sobre el tema "Asymmetric synthesis. Lactones"

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Publicado: 4 de junio de 2021
Última modificación: 8 de febrero de 2022

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1

Mondon, M. y J. Gesson. "Asymmetric Synthesis of Styryl-Lactones". Current Organic Synthesis 3, n.º 1 (1 de febrero de 2006): 41–75. http://dx.doi.org/10.2174/157017906775473966.

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2

Shimotori, Yasutaka, Kazuki Sekine y Tetsuo Miyakoshi. "Asymmetric synthesis ofδ-lactones with lipase catalyst". Flavour and Fragrance Journal 22, n.º 6 (2007): 531–39. http://dx.doi.org/10.1002/ffj.1836.

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3

Wong, Leon S. M., Kathleen A. Turner, Jonathan M. White, Andrew B. Holmes y John H. Ryan. "Asymmetric Synthesis of a Hydroxylated Nine-membered Lactone from Tartaric Acid using the Claisen Rearrangement". Australian Journal of Chemistry 63, n.º 3 (2010): 529. http://dx.doi.org/10.1071/ch09637.

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The synthesis of a hydroxylated vinyl-appended lactone, in five synthetic steps from tartaric acid, is reported. The C2-symmetrical bis-vinyl diol 12 was converted into the ketene acetal 14 via methylenation of the cyclic carbonate 13 or thermal elimination of benzeneselenenic acid from the selenoxide 17. In both cases, the in situ generated ketene acetal 14 underwent spontaneous Claisen rearrangement to give the nine-membered lactone (+)-15. Lactones of this type are potentially advanced precursors to simplified eleutherobin analogues or other medium-ring lactone natural products.
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4

Li, Yanjun y Taeko Izumi. "Asymmetric Synthesis of Chiral δ-lactones using BINAP-ruthenium(II) Complexes Hydrogenation Catalysts". Journal of Chemical Research 2002, n.º 11 (noviembre de 2002): 567–69. http://dx.doi.org/10.3184/030823402103170790.

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Asymmetric hydrogenation of keto-acids was accomplished by catalytic amounts of BINAP-ruthenium complexes to afford the corresponding δ-lactones in high yields. The optical purity of the synthesised δ-lactones was determined by chiralcel (OD) in the 9–56% range.
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5

Yang, Jiaxin, Xiuxiu Li, Cai You, Shuailong Li, Yu-Qing Guan, Hui Lv y Xumu Zhang. "Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds". Organic & Biomolecular Chemistry 18, n.º 5 (2020): 856–59. http://dx.doi.org/10.1039/c9ob02536g.

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6

Ray Choudhury, Abhijnan y Santanu Mukherjee. "Deconjugated butenolide: a versatile building block for asymmetric catalysis". Chemical Society Reviews 49, n.º 18 (2020): 6755–88. http://dx.doi.org/10.1039/c9cs00346k.

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Deconjugated butenolides have emerged as a popular synthon for the enantioselective synthesis of γ-lactones. This review provides a comprehensive overview on the catalytic asymmetric reactions of deconjugated butenolides reported till date.
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7

Nagao, Yoshimitsu, Toshiaki Tohjo, Masahito Ochiai y Motoo Shiro. "Expeditious Asymmetric Synthesis of Optically Pure δ-Lactones Bearing Consecutive Three Asymmetric Centers". Chemistry Letters 21, n.º 2 (febrero de 1992): 335–38. http://dx.doi.org/10.1246/cl.1992.335.

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8

Marco, J. Alberto y Miguel Carda. "Stereoselective Synthesis of Five Biologically Active, Naturally Occurring Medium and Large Ring Lactones". Natural Product Communications 6, n.º 4 (abril de 2011): 1934578X1100600. http://dx.doi.org/10.1177/1934578x1100600411.

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Stereoselective syntheses of five naturally occurring, pharmacologically active medium and large ring lactones are described. Key synthetic methods used were, depending on the cases, olefin metatheses, asymmetric allylations and C-glycosidations.
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9

Gaikwad, Ravindra D., Monica D. Rane y Sujata V. Bhat. "Asymmetric synthesis of (6R)-4-hydroxy-6-substituted-δ-lactones". Tetrahedron: Asymmetry 28, n.º 1 (enero de 2017): 181–85. http://dx.doi.org/10.1016/j.tetasy.2016.12.006.

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10

Peed, Jennifer, Ignacio Periñán Domínguez, Iwan R. Davies, Matt Cheeseman, James E. Taylor, Gabriele Kociok-Köhn y Steven D. Bull. "Asymmetric Synthesis of Chiral δ-Lactones Containing Multiple Contiguous Stereocenters". Organic Letters 13, n.º 14 (15 de julio de 2011): 3592–95. http://dx.doi.org/10.1021/ol2012023.

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11

Campagne, J. M., B. Bazán-Tejeda, G. Bluet y G. Broustal. "Cu-Catalyzed Asymmetric Synthesis of α,β-Unsaturated δ-Lactones". Synfacts 2007, n.º 1 (enero de 2007): 0073. http://dx.doi.org/10.1055/s-2006-955732.

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12

Xiong, Zhichao, Jiangyan Tian, Peng Xue, Xumu Zhang y Hui Lv. "Enantioselective synthesis of chiral multicyclic γ-lactones via dynamic kinetic resolution of racemic γ-keto carboxylic acids". Organic Chemistry Frontiers 7, n.º 1 (2020): 104–8. http://dx.doi.org/10.1039/c9qo01047e.

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13

Ramachandran, P. Veeraraghavan, M. Venkat Ram Reddy y Herbert C. Brown. "Tandem allylboration-ring-closing metathesis reactions for the preparation of biologically active molecules". Pure and Applied Chemistry 75, n.º 9 (1 de enero de 2003): 1263–75. http://dx.doi.org/10.1351/pac200375091263.

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The development of asymmetric synthesis during the past two decades aided organic chemists considerably in the synthesis of complex natural products. Organoborane chemistry continues to play an important role in asymmetric synthesis. One of the important reactions that has become very common in the arsenal of synthetic chemists is allylboration and related reactions. Another important reaction that has recently attained enormous importance in organic chemistry is the ring-closing metathesis (RCM) reaction. Indeed, a combination of allylboration and RCM reactions provides an excellent route to cyclic ethers, lactones, lactams, etc. Herein, we describe a sequential asymmetric allylboration and RCM reaction protocol that has been utilized for the synthesis of several alpha-pyrone-containing natural products,particularly biologically active molecules.
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14

Helmchen, G., Martin Ernst y G. Paradies. "Application of allylic substitutions in natural products synthesis". Pure and Applied Chemistry 76, n.º 3 (1 de enero de 2004): 495–505. http://dx.doi.org/10.1351/pac200476030495.

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Synthesis routes are described, allowing all known jasmonoids as well as their enantiomers to be synthesized in enantiomerically and diastereomerically pure form. The routes are based on a set of closely related lactones containing an electrophilic allylic moiety, which are accessible via asymmetric Pd-catalyzed allylic alkylation. Regio- and diastereoselective SN2'-anti-reactions of the electrophilic lactones with organocopper compounds furnished 2,3-cis-disubstituted cyclopentenones, which were further transformed into the target compounds, i.e., 12-oxophytodienoic acid (12-OPDA) in excellent overall yields. The methodology also allowed iridoids and isoprostanes to be prepared. The configuration of an Archaea membrane lipid constituent containing cyclopentane rings was determined by total synthesis of a diol that was also obtained by degradation of the natural product.
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15

Zhou, Wei-Shan y Zhi-Cai Yang. "Asymmetric Total Synthesis of Antitumor Styryl Lactones and Related Natural Products". HETEROCYCLES 45, n.º 2 (1997): 367. http://dx.doi.org/10.3987/rev-96-487.

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16

Chen, Shi, Ahmad A. Ibrahim, Nicholas J. Peraino, Divya Nalla, Mukulesh Mondal, Maxwell Van Raaphorst y Nessan J. Kerrigan. "Catalytic Asymmetric Synthesis of Ketene Heterodimer β-Lactones: Scope and Limitations". Journal of Organic Chemistry 81, n.º 17 (12 de agosto de 2016): 7824–37. http://dx.doi.org/10.1021/acs.joc.6b01481.

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17

Paju, Anne, Marit Laos, Artur Jõgi, Malle Päri, Raissa Jäälaid, Tõnis Pehk, Tõnis Kanger y Margus Lopp. "Asymmetric synthesis of 2-alkyl-substituted 2-hydroxyglutaric acid γ-lactones". Tetrahedron Letters 47, n.º 26 (junio de 2006): 4491–93. http://dx.doi.org/10.1016/j.tetlet.2006.04.013.

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18

NAGAO, Y., T. TOHJO, M. OCHIAI y M. SHIRO. "ChemInform Abstract: Expeditious Asymmetric Synthesis of Optically Pure δ-Lactones Bearing Consecutive Three Asymmetric Centers." ChemInform 23, n.º 50 (1 de septiembre de 2010): no. http://dx.doi.org/10.1002/chin.199250076.

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19

Bringmann, Gerhard, Robert-Michael Pfeifer, Christian Rummey, Thomas Pabst, Dirk Leusser y Dietmar Stalke. "Structural Investigation of a Configurationally Stable Seven-Membered Bridged Biaryl of Relevance for Atroposelective Biaryl Syntheses*". Zeitschrift für Naturforschung B 58, n.º 2-3 (1 de marzo de 2003): 231–36. http://dx.doi.org/10.1515/znb-2003-2-305.

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The atroposelective ring opening of lactone-bridged biaryl systems is the key step in the total synthesis of a series of axially chiral biaryl natural products and useful reagents or catalysts for asymmetric synthesis. For a more in-depth understanding of the mechanism and stereochemical course of this remarkable cleavage reaction, a seven-membered ether analog of such useful biaryl lactones has been investigated structurally, both experimentally, by X-ray diffraction analysis, and by ab initio calculations (B3LYP/6-31G*). In a nearly perfect agreement, both methods show that these seven-membered bridged biaryls do not constitute helicene-like distorted molecules, but ‘true’ biaryls, whose sufficiently long lactone or ether bridge allows the two aromatic systems to adopt a large dihedral angle to each other, without any noticeable deviation from planarity for the two aromatic systems - in contrast to related six-membered analogs, which can rather be considered as helicene-like twisted polycyclic systems.
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20

Kernen, Philippe y Pierre Vogel. "Total asymmetric synthesis of polypropionate fragments and doubly branched heptono-1,4-lactones". Tetrahedron Letters 34, n.º 15 (abril de 1993): 2473–76. http://dx.doi.org/10.1016/s0040-4039(00)60444-6.

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21

KAWAKAMI, Yukio, Jun HIRATAKE, Yukio YAMAMOTO y Jun''ichi ODA. "An asymmetric synthesis of lactones from cyclic acid anhydrides with chiral binaphthyldiamines." Agricultural and Biological Chemistry 50, n.º 3 (1986): 693–98. http://dx.doi.org/10.1271/bbb1961.50.693.

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22

Liu, Qiang, Sun Li, Xiang-Yu Chen, Kari Rissanen y Dieter Enders. "Asymmetric Synthesis of Spiro-oxindole-ε-lactones through N-Heterocyclic Carbene Catalysis". Organic Letters 20, n.º 12 (7 de junio de 2018): 3622–26. http://dx.doi.org/10.1021/acs.orglett.8b01400.

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23

Chen, Shi, Mukulesh Mondal, Ahmad A. Ibrahim, Kraig A. Wheeler y Nessan J. Kerrigan. "Phosphine-Catalyzed Asymmetric Synthesis of β-Lactones from Disubstituted Ketenes and Aldehydes". Journal of Organic Chemistry 79, n.º 11 (8 de mayo de 2014): 4920–29. http://dx.doi.org/10.1021/jo500486e.

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24

Mondal, Mukulesh, Ahmad A. Ibrahim, Kraig A. Wheeler y Nessan J. Kerrigan. "Phosphine-Catalyzed Asymmetric Synthesis of β-Lactones from Arylketoketenes and Aromatic Aldehydes". Organic Letters 12, n.º 8 (16 de abril de 2010): 1664–67. http://dx.doi.org/10.1021/ol100075m.

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25

Peed, Jennifer, Ignacio Perinan Dominguez, Iwan R. Davies, Matt Cheeseman, James E. Taylor, Gabriele Kociok-Koehn y Steven D. Bull. "ChemInform Abstract: Asymmetric Synthesis of Chiral δ-Lactones Containing Multiple Contiguous Stereocenters." ChemInform 42, n.º 48 (3 de noviembre de 2011): no. http://dx.doi.org/10.1002/chin.201148140.

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26

Kawakami, Yukio, Jun Hiratake, Yukio Yamamoto y Jun’ichi Oda. "An Asymmetric Synthesis of Lactones from Cyclic Acid Anhydrides with Chiral Binaphthyldiamines". Agricultural and Biological Chemistry 50, n.º 3 (marzo de 1986): 693–98. http://dx.doi.org/10.1080/00021369.1986.10867431.

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27

Dong, Chune y Howard Alper. "Catalytic Asymmetric Cyclocarbonylation ofo-Isopropenylphenols: Enantioselective Synthesis of Six-Membered Ring Lactones". Journal of Organic Chemistry 69, n.º 15 (julio de 2004): 5011–14. http://dx.doi.org/10.1021/jo040109f.

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28

Hao, Xiaoyu, Xiaohua Liu, Wei Li, Fei Tan, Yangyang Chu, Xiaohu Zhao, Lili Lin y Xiaoming Feng. "Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones". Organic Letters 16, n.º 1 (4 de diciembre de 2013): 134–37. http://dx.doi.org/10.1021/ol4031217.

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29

Doda, Sai Reddy, Avula Raghavendar, Sharath Babu Haridasyam, Chandra Shekar Putta, Bhattu Kanakadurga rao y Sudhakar Kadari. "Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol". Heterocyclic Communications 25, n.º 1 (17 de mayo de 2019): 78–84. http://dx.doi.org/10.1515/hc-2019-0015.

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AbstractAn efficient, short and, a convenient asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol (2) and zeaenol (1) have been achieved in 7 and 9 linear steps with the high overall yield of 32% and 21% respectively, from the known intermediate 13. Mitsunobu inversion, De Brabander’s protocol for macrolactonisation, Heck cross-coupling, diastereoselective alkyne aldehyde coupling and Ohira–Bestmann alkynylation are the key reactions.
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30

Trova, Michael P., Allan Wissner, Wellington T. Casscles y Grace C. Hsu. "Asymmetric synthesis of cis- and trans-γ-lactones useful in HIV-1 protease inhibitor synthesis". Bioorganic & Medicinal Chemistry Letters 4, n.º 7 (enero de 1994): 903–6. http://dx.doi.org/10.1016/s0960-894x(01)80260-2.

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31

Curran, Dennis P. y Sung-Bo Ko. "Synthesis of Optically Active .alpha.-Hydroxy Lactones by Sharpless Asymmetric Dihydroxylations of Ketene Acetals, Enol Ethers, and Ene Lactones". Journal of Organic Chemistry 59, n.º 21 (octubre de 1994): 6139–41. http://dx.doi.org/10.1021/jo00100a005.

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32

Hu, Bin y Li Deng. "Direct Catalytic Asymmetric Synthesis of Trifluoromethylated γ-Amino Esters/Lactones via Umpolung Strategy". Journal of Organic Chemistry 84, n.º 2 (13 de diciembre de 2018): 994–1005. http://dx.doi.org/10.1021/acs.joc.8b02893.

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33

Peraino, Nicholas J., Han-Jen Ho, Mukulesh Mondal y Nessan J. Kerrigan. "Asymmetric synthesis of γ-lactones through reaction of sulfoxonium ylides, aldehydes, and ketenes". Tetrahedron Letters 55, n.º 30 (julio de 2014): 4260–63. http://dx.doi.org/10.1016/j.tetlet.2014.05.130.

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34

YANG, Z. C. y W. S. ZHOU. "ChemInform Abstract: Asymmetric Total Synthesis of Antitumor Styryl Lactones and Related Natural Products". ChemInform 28, n.º 33 (3 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199733346.

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35

Kull, Thomas y René Peters. "Contact Ion Pair Directed Lewis Acid Catalysis: Asymmetric Synthesis oftrans‐Configured β‐Lactones". Angewandte Chemie International Edition 47, n.º 29 (7 de julio de 2008): 5461–64. http://dx.doi.org/10.1002/anie.200801143.

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36

Raffaelli, Barbara, Kristiina Wähälä y Tapio Hase. "Asymmetric synthesis, stereochemistry and rearrangement reactions of naturally occurring 7′-hydroxylignano-9,9′-lactones". Org. Biomol. Chem. 4, n.º 2 (2006): 331–41. http://dx.doi.org/10.1039/b513303c.

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37

Zemribo, Ronald y Daniel Romo. "Highly diastereoselective [2+2] cycloadditions via chelation control: Asymmetric synthesis of β-lactones". Tetrahedron Letters 36, n.º 24 (junio de 1995): 4159–62. http://dx.doi.org/10.1016/0040-4039(95)00716-p.

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38

Bourboula, Asimina, Dimitris Limnios, Maroula G. Kokotou, Olga G. Mountanea y George Kokotos. "Enantioselective Organocatalysis-Based Synthesis of 3-Hydroxy Fatty Acids and Fatty γ-Lactones". Molecules 24, n.º 11 (31 de mayo de 2019): 2081. http://dx.doi.org/10.3390/molecules24112081.

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3-Hydroxy fatty acids have attracted the interest of researchers, since some of them may interact with free fatty acid receptors more effectively than their non-hydroxylated counterparts and their determination in plasma provides diagnostic information regarding mitochondrial deficiency. We present here the development of a convenient and general methodology for the asymmetric synthesis of 3-hydroxy fatty acids. The enantioselective organocatalytic synthesis of terminal epoxides, starting from long chain aldehydes, is the key-step of our methodology, followed by ring opening with vinylmagnesium bromide. Ozonolysis and subsequent oxidation leads to the target products. MacMillan’s third generation imidazolidinone organocatalyst has been employed for the epoxide formation, ensuring products in high enantiomeric purity. Furthermore, a route for the incorporation of deuterium on the carbon atom carrying the hydroxy group was developed allowing the synthesis of deuterated derivatives, which may be useful in biological studies and in mass spectrometry studies. In addition, the synthesis of fatty γ-lactones, corresponding to 4-hydroxy fatty acids, was also explored.
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39

Hao, Xiaoyu, Xiaohua Liu, Wei Li, Fei Tan, Yangyang Chu, Xiaohu Zhao, Lili Lin y Xiaoming Feng. "ChemInform Abstract: Chiral Lewis Acid Catalyzed Asymmetric Cycloadditions of Disubstituted Ketenes for the Synthesis of β-Lactones and δ-Lactones." ChemInform 45, n.º 24 (2 de junio de 2014): no. http://dx.doi.org/10.1002/chin.201424031.

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40

Enders, Dieter, Juan Vázquez y Gerhard Raabe. "Formaldehyde SAMP-Hydrazone as a Neutral Formyl Anion Equivalent: Asymmetric Synthesis of Substituted β-Formyl δ-Lactones and Furofuran Lactones". European Journal of Organic Chemistry 2000, n.º 6 (marzo de 2000): 893–901. http://dx.doi.org/10.1002/(sici)1099-0690(200003)2000:6<893::aid-ejoc893>3.0.co;2-u.

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41

Cai, Quan, Xu-Ge Si y Zhi-Mao Zhang. "Asymmetric Inverse-Electron-Demand Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis". Synlett 32, n.º 10 (24 de enero de 2021): 947–54. http://dx.doi.org/10.1055/a-1371-4391.

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AbstractDiels–Alder reactions of 2-pyrones with alkenes can provide highly functionalized [2,2,2]-bicyclic lactones under mild reaction conditions. Synthetic utilizations of these reactions have been well demonstrated in natural-product synthesis. Although several catalytic asymmetric strategies have been realized, current research in this area is still largely underdeveloped. Recent advances in enantioselective inverse-electron-demand Diels–Alder reactions with Lewis acid catalysis are reviewed.1 Introduction2 State of the Art of Enantioselective Diels–Alder Reactions of 2-Pyrones by Lewis Acid Catalysis3 Enantioselective Synthesis of Arene cis-Dihydrodiols by Diels–­Alder/Retro-Diels–Alder Reactions of 2-Pyrones4 Enantioselective Synthesis of cis-Decalin Derivatives by Diels–­Alder Reactions of 2-Pyrones5 Conclusions
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42

Buttero, Paola y Deborah Montrasio. "Tricarbonyl(h6-Arene)Chromium(0) Complexes as Chiral Auxiliaries: Asymmetric Synthesis of b-Lactones". Molecules 6, n.º 12 (16 de enero de 2001): 13–20. http://dx.doi.org/10.3390/60100013.

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43

Enders, Dieter y Mareile Haas. "Asymmetric Synthesis of 4,5-Disubstituted 3-Hydroxy δ-Lactones: Prelactone B and Prelactone V". Synlett, n.º 14 (2003): 2182–84. http://dx.doi.org/10.1055/s-2003-42060.

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44

Cortez, Guillermo S., Reginald L. Tennyson y Daniel Romo. "Intramolecular, Nucleophile-Catalyzed Aldol-Lactonization (NCAL) Reactions: Catalytic, Asymmetric Synthesis of Bicyclic β-Lactones". Journal of the American Chemical Society 123, n.º 32 (agosto de 2001): 7945–46. http://dx.doi.org/10.1021/ja016134+.

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45

Chen, Shi, Mukulesh Mondal, Ahmad A. Ibrahim, Kraig A. Wheeler y Nessan J. Kerrigan. "ChemInform Abstract: Phosphine-Catalyzed Asymmetric Synthesis of β-Lactones from Disubstituted Ketenes and Aldehydes." ChemInform 45, n.º 48 (13 de noviembre de 2014): no. http://dx.doi.org/10.1002/chin.201448106.

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46

Wang, Yang, Lingling Deng, Jie Zhou, Xiaochen Wang, Haibo Mei, Jianlin Han y Yi Pan. "Synthesis of Chiral Sulfonyl Lactones via Copper-Catalyzed Asymmetric Radical Reaction of DABCO⋅(SO2 )". Advanced Synthesis & Catalysis 360, n.º 6 (15 de enero de 2018): 1060–65. http://dx.doi.org/10.1002/adsc.201701532.

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47

Mondal, Mukulesh, Ahmad A. Ibrahim, Kraig A. Wheeler y Nessan J. Kerrigan. "ChemInform Abstract: Phosphine-Catalyzed Asymmetric Synthesis of β-Lactones from Arylketoketenes and Aromatic Aldehydes." ChemInform 41, n.º 35 (5 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.201035108.

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48

Davies, Stephen G., Rebecca L. Nicholson y Andrew D. Smith. "Double diastereoselective SuperQuat glycolate aldol reactions: Application to the asymmetric synthesis of polyfunctionalised lactones". Organic & Biomolecular Chemistry 2, n.º 22 (2004): 3385. http://dx.doi.org/10.1039/b411724g.

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49

Marino, J. P. y Roberto Fernández de la Pradilla. "Stereospecific synthesis of γ-butyrolactones from acyclic vinyl sulfoxides: an asymmetric synthesis of optically pure oak lactones". Tetrahedron Letters 26, n.º 44 (enero de 1985): 5381–84. http://dx.doi.org/10.1016/s0040-4039(00)98213-3.

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50

TROVA, M. P., A. WISSNER, W. T. JUN CASSCLES y G. C. HSU. "ChemInform Abstract: Asymmetric Synthesis of cis- and trans-γ-Lactones Useful in HIV- 1 Protease Inhibitor Synthesis." ChemInform 25, n.º 40 (18 de agosto de 2010): no. http://dx.doi.org/10.1002/chin.199440208.

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