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Journal articles on the topic 'N,o-acetal'

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1

Kantlehner, Willi, Birgit Heckel, and Jochen Mezger. "Orthoamide und Iminiumsalze, CI. Umsetzungen von N,N,N′,N′-Tetramethylharnstoffdiethylacetal mit CH2-aciden Verbindungen." Zeitschrift für Naturforschung B 75, no. 9-10 (2020): 865–80. http://dx.doi.org/10.1515/znb-2020-0072.

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AbstractN,N,N′,N′-Tetramethylurea diethylacetal reacts with CH2-acidic compounds as benzylcyanide, cyanoacetic acid derivatives malonodinitrile and nitromethane to give ketene aminals or ketene-O,N-acetales. Low polar solvents favour mostly the formation of ketenaminals. The yields of ketenaminals and ketene-O,N-acetals can be improved in some cases by addition of trimethylsilyldimethylamine. The reactions of the urea acetal with diethylmalonate, ore acetyl acetone, stops at the stage of the N,N′,N″-permethylated guanidinium salts with carbanionic counterions. The formation of bis(dimethylamin
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2

Kim, Minjun, Jaebong Jang, Goyoung Choi та ін. "Conversion of Medium-Sized Lactams to α-Vinyl or α-Acetylenyl Azacycles via N,O-Acetal TMS Ethers". Molecules 23, № 11 (2018): 3023. http://dx.doi.org/10.3390/molecules23113023.

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α-Vinyl or α-acetylenyl azacycles were easily synthesized from 7- to 9-membered lactams and 6- to 9-membered lactams via N,O-acetal trimethylsilyl (TMS) ethers. Organocopper and organostannane reagents afforded reasonable yields for the respective N-acyliminium ion vinylation and acetylenylation intermediates generated from N,O-acetal TMS ethers in the presence of a Lewis acid.
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3

MASLINSKA-SOLICH, JOLANTA, EDYTA GIBAS, and SYLWIA KUKOWKA. "The formation of macrocyclic compounds with O,O- and O,N-acetal units." Polimery 50, no. 07/08 (2005): 509–19. http://dx.doi.org/10.14314/polimery.2005.509.

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4

Maslov, M. A., N. G. Morosova, I. M. Senan, and G. A. Serebrennikova. "Synthesis of cationic lipid transfection agents with O,O- or N,O-acetal linkages." Russian Journal of Bioorganic Chemistry 35, no. 5 (2009): 628–32. http://dx.doi.org/10.1134/s1068162009050148.

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5

Lee, Won-Il, Jong-Wha Jung, Jaebong Jang, Hwayoung Yun, and Young-Ger Suh. "Synthesis of 5,6-dihydrophenanthridines via N,O-acetal TMS ethers." Tetrahedron Letters 54, no. 38 (2013): 5167–71. http://dx.doi.org/10.1016/j.tetlet.2013.07.037.

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6

Wang, Pengcheng, Ruirui Yu, Sajjad Ali, et al. "Silver Catalyzed Decarbonylative [3 + 2] Cycloaddition of Cyclobutenediones and Formamides." Molecules 26, no. 10 (2021): 2974. http://dx.doi.org/10.3390/molecules26102974.

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As an important moiety in natural products, N,O-acetal has attracted wide attention in the past few years. An efficient method to construct N,O-acetal has been developed. Using silver catalyst, cyclobutenediones were smoothly converted to the corresponding γ-aminobutenolides in the presence of formamides, in which cyclobutenediones likely proceed with a key decarbonylative [3 + 2] cycloaddition process. In this way, a series of products with varied substituents were isolated in moderate yield and fully characterized.
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7

van der Pijl, Ferdi, Floris L. van Delft, and Floris P. J. T. Rutjes. "Synthesis and functionalization of bicyclic N,O-acetal scaffolds from furfural." Bioorganic & Medicinal Chemistry 23, no. 11 (2015): 2721–29. http://dx.doi.org/10.1016/j.bmc.2014.12.045.

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8

Qiu, Xianfan, Liugen Xu, Shuxia Wang, et al. "Copper-catalyzed borylative aminomethylation of C–C double and triple bonds with N,O-acetal." Chemical Communications 57, no. 26 (2021): 3279–82. http://dx.doi.org/10.1039/d1cc00093d.

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9

Ibrahim, Sherif M. S., Koushik Banerjee, Kara A. Slater, and Gregory K. Friestad. "A Tamao–Fleming oxidation route to dipeptides bearing N,O-acetal functionality." Tetrahedron Letters 58, no. 52 (2017): 4864–66. http://dx.doi.org/10.1016/j.tetlet.2017.11.036.

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10

Lee, Won-Il, Jong-Wha Jung, Jaebong Jang, Jaebong Yun, Hwayoung Yun, and Young-Ger Suh. "ChemInform Abstract: Synthesis of 5,6-Dihydrophenanthridines via N,O-Acetal TMS Ethers." ChemInform 45, no. 3 (2014): no. http://dx.doi.org/10.1002/chin.201403180.

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11

Kimatrai, M., O. Cruz-Lopez, M. E. Garcia-Rubino, F. Morales, V. Gomez-Perez, and J. M. Campos. "Neighboring-Group Participation Involving the Oxygen Atom of the O,O- or O,N-acetal Functional Groups." Current Organic Chemistry 14, no. 14 (2010): 1461–77. http://dx.doi.org/10.2174/138527210791616777.

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12

Krasnaya, Zh A., Yu V. Smirnova, and V. S. Bogdanov. "Reaction of dimethylaminomethylenemalonaldehyde bis-N,O-acetal with ketones. A novel route to N-methylpyrroles." Chemistry of Heterocyclic Compounds 32, no. 5 (1996): 560–67. http://dx.doi.org/10.1007/bf01164785.

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13

Möhrle, Hans, and Heinz Dwuletzki. "Lactam-acetale als potentielle Enamin-Synthone in Heterocyclensynthesen, 1. Das Lactam-acetal/Keten-N,O-acetal-System in 1,3-dipolarer Cycloaddition." Chemische Berichte 119, no. 12 (1986): 3591–99. http://dx.doi.org/10.1002/cber.19861191208.

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14

Li, Ji-Yao, Zhi-Long Li, Wei-Wei Zhao, Yan-Kai Liu, Zhi-Ping Tong, and Rui Tan. "One-pot, highly efficient, asymmetric synthesis of ring-fused piperidine derivatives bearing N,O- or N,N-acetal moieties." Organic & Biomolecular Chemistry 14, no. 8 (2016): 2444–53. http://dx.doi.org/10.1039/c5ob02571k.

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15

Zhang, Yan-Hui, Rong Liu, and Bo Liu. "Total synthesis of nannocystin Ax." Chemical Communications 53, no. 40 (2017): 5549–52. http://dx.doi.org/10.1039/c7cc00469a.

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Total synthesis of nannocystin Ax has been accomplished concisely. The key elements in this total synthesis feature Kobayashi's remote asymmetric induction with vinylketene silyl N,O-acetal, Roush's asymmetric crotylboration of aldehyde, Mitsunobu's esterification and macrocyclization via Stille cross-coupling.
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16

Martens, Thierry, Florence Souquet та Jacques royer. "Anodic oxidation of the N-cyanomethyl-oxazolidine system: Regioselective chlorination α to the N,O-acetal function". Tetrahedron Letters 35, № 37 (1994): 6879–82. http://dx.doi.org/10.1016/0040-4039(94)85030-5.

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17

Hosokawa, Seijiro, and Haruka Sato. "Synthesis of the C1–C17 Segment of Bafilomycin N." Synlett 30, no. 05 (2019): 577–80. http://dx.doi.org/10.1055/s-0037-1611727.

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The C1–C17 segment of bafilomycin N has been synthesized. The C1–C11 segment was synthesized by the anti-selective vinylogous Mukaiyama aldol reaction with a chiral vinylketene silyl N,O-acetal and the Horner–Wadsworth–Emmons reaction, whereas C12–C17 was constructed by the syn-selective vinylogous Mukaiyama aldol reaction and the Jung’s semipinacol rearrangement. Those segments were connected by the Stille coupling to afford the C1–C17 segment.
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18

De Silva, Hondamuni I., Yingquan Song, William P. Henry, and Charles U. Pittman. "Ring size and substituent steric effects in cyclic ketene-N,O/S-acetal trifluoroacetylations." Tetrahedron Letters 53, no. 24 (2012): 2965–70. http://dx.doi.org/10.1016/j.tetlet.2012.03.068.

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19

Ohsawa, Kosuke, Shota Ochiai, Junya Kubota, and Takayuki Doi. "Gold-Catalyzed Amide/Carbamate-Linked N,O-Acetal Formation with Bulky Amides and Alcohols." Journal of Organic Chemistry 86, no. 1 (2020): 1281–91. http://dx.doi.org/10.1021/acs.joc.0c02640.

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20

Huang, Yung-tzung, and Kevin D. Moeller. "Anodic cyclization reactions: probing the chemistry of N,O-ketene acetal derived radical cations." Tetrahedron 62, no. 27 (2006): 6536–50. http://dx.doi.org/10.1016/j.tet.2006.04.009.

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21

Xi, Xin, Ximei Zhao, Feng Zhu та ін. "Synthesis and Insecticidal Activity of β-Dihydroagarofuran Acetal Derivatives". Natural Product Communications 13, № 4 (2018): 1934578X1801300. http://dx.doi.org/10.1177/1934578x1801300404.

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To search for improved insecticidal compounds based on β-dihydroagarofuran sesquiterpenoids, forty-four β-dihydroagarofuran acetal derivatives were designed and synthesized. Insecticidal activities and structure-activity relationship of these target compounds were evaluated. Some of the newly synthesized β-dihydroagarofuran acetal compounds were found to show higher insecticidal activity against sixth-instar larvae of Mythimna separate. Especially, compounds 2.2.9, 2.2.10, 2.2.11, 2.3.4, 2.3.6, 2.3.7, 2.5.4, 2.5.7 had great insecticidal activities with lower LD50 than that of the positive cont
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22

Sagawa, Naoya, Hiroki Moriya, and Seijiro Hosokawa. "Syn Selective Vinylogous Mukaiyama Aldol Reaction Using Z,E-Vinylketene N,O-Acetal with Acetals." Organic Letters 19, no. 1 (2016): 250–53. http://dx.doi.org/10.1021/acs.orglett.6b03549.

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23

Song, Yingquan, Hondamuni I. De Silva, William P. Henry, Guozhong Ye, Sabornie Chatterjee, and Charles U. Pittman. "Regiochemistry of an ambident cyclic ketene-N,O-acetal nucleophile and its anion toward electrophiles." Tetrahedron Letters 52, no. 35 (2011): 4507–11. http://dx.doi.org/10.1016/j.tetlet.2011.06.023.

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24

Weaver, Matthew J., Michael J. Campbell, Chun Li, and Nicholas R. Natale. "Ethyl 5-methyl-3-[11-(pyridin-2-yl)-6,11-dihydro-6,11-epoxydibenzo[b,e]oxepin-6-yl]isoxazole-4-carboxylate: a bicyclic acetal from the rearrangement of an anthracenyl isoxazole." Acta Crystallographica Section E Crystallographic Communications 76, no. 12 (2020): 1818–22. http://dx.doi.org/10.1107/s2056989020014358.

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The title compound, C26H20N2O5, is a rearrangement product of an o-pyridinyl anthracenyl isoxazole ester. It features a bicyclic acetal structure, which has two extended almost co-planar ring systems, which subtend a fold angle of 102.17 (5)°. In the crystal, the molecules are closely knitted together through C—H...N and C—H...O hydrogen bonds and form chains of alternating enantiomers propagating along the c-axis direction.
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25

Marsh, R. E., W. P. Schaefer, K. L. Widdowson, and A. G. Myers. "Structure of an anti-aldol addition product of benzaldehyde and a pseudoephedrine-derived O-silyl ketene N,O-acetal." Acta Crystallographica Section C Crystal Structure Communications 48, no. 11 (1992): 1948–51. http://dx.doi.org/10.1107/s0108270192002233.

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26

Marsh, R. E., W. P. Schaefer, S. E. Kephart, and A. G. Myers. "Structure of a syn-aldol addition product of benzaldehyde and a prolinol-derived O-silacyclopentyl ketene N,O-acetal." Acta Crystallographica Section C Crystal Structure Communications 49, no. 1 (1993): 185–88. http://dx.doi.org/10.1107/s0108270192008825.

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27

Oppolzer, Wolfgang, Christian Starkemann, Inès Rodriguez, and Gérald Bernardinelli. "Enantiomerically pure, crystalline ‘anti’-aldols from N-acylbornanesultams: aldolization and structure of intermediate t-butyldimethylsilyl-N,O-ketene acetal." Tetrahedron Letters 32, no. 1 (1991): 61–64. http://dx.doi.org/10.1016/s0040-4039(00)71218-4.

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28

MARTENS, T., F. SOUQUET та J. ROYER. "ChemInform Abstract: Anodic Oxidation of the N-Cyanomethyl-oxazolidine System: Regioselective Chlorination α to the N,O-Acetal Function." ChemInform 26, № 7 (2010): no. http://dx.doi.org/10.1002/chin.199507079.

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29

Yanai, Hikaru, and Takeo Taguchi. "Novel defluorinative alkylation of trifluoroacetaldehyde N,O-acetal derivatives and its application to multi-component reaction." Chem. Commun., no. 9 (2009): 1034–36. http://dx.doi.org/10.1039/b817599c.

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30

Suh, Young-Ger, Jaebong Jang, Hwayoung Yun, et al. "ChemInform Abstract: Expedient Synthesis of Chiral Homoallylamines via N,O-Acetal TMS Ethers and Its Application." ChemInform 43, no. 12 (2012): no. http://dx.doi.org/10.1002/chin.201212064.

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31

TSUKAMOTO, T., та T. KITAZUME. "ChemInform Abstract: Lewis Acid-Promoted Reaction of β,β-Difluorinated N,O-Acetal with Silylated Nucleophiles." ChemInform 24, № 11 (2010): no. http://dx.doi.org/10.1002/chin.199311098.

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32

Mukaeda, Yuki, Takuya Kato, and Seijiro Hosokawa. "ChemInform Abstract: Syn-Selective Kobayashi Aldol Reaction Using the E,E-Vinylketene Silyl N,O-Acetal." ChemInform 44, no. 11 (2013): no. http://dx.doi.org/10.1002/chin.201311035.

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33

Grindley, T. Bruce, and Srihari Kusuma. "Kinetic benzylidenation. Part II. Rearrangement of the kinetic products from benzylidenation of aldose diethyl dithioacetals." Canadian Journal of Chemistry 64, no. 12 (1986): 2397–403. http://dx.doi.org/10.1139/v86-396.

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Terminal five-membered O-benzylidene derivatives of aldose diethyl dithioacetals can be rearranged at room temperature in N,N-dimethylformamide, often in high yields. Derivatives with the arabino configuration for their three terminal secondary hydroxyl groups, i.e. D-glucose, D-mannose, and D-arabinose derivatives, rearranged to structures containing terminal six-membered O-benzylidene rings. 4,5-O-Benzylidene-D-ribose diethyl dithioacetal rearranged chiefly to the 2,4 isomer, which was obtained by crystallization. Chromatography yielded some of the 3,5 isomer. 5,6-O-Benzylidene-D-galactose d
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34

Pingali, Subramanya, James P. Donahue, and Florastina Payton-Stewart. "Weak C—H...X(X= O, N) hydrogen bonds in the crystal structure of dihydroberberine." Acta Crystallographica Section C Structural Chemistry 70, no. 4 (2014): 388–91. http://dx.doi.org/10.1107/s2053229614003751.

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Dihydroberberine (systematic name: 9,10-dimethoxy-6,8-dihydro-5H-1,3-dioxolo[4,5-g]isoquinolino[3,2-a]isoquinoline), C20H19NO4, a reduced form of pharmacologically important berberine, crystallizes from ethanol without interstitial solvent. The molecule shows a dihedral angle of 27.94 (5)° between the two arene rings at the ends of the molecule, owing to the partial saturation of the inner quinolizine ring system. Although lacking classical O—H or N—H donors, the packing in the crystalline state is clearly governed by C—H...N and C—H...O hydrogen bonds involving the two acetal-type C—H bonds o
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35

MARSH, R. E., W. P. SCHAEFER, K. L. WIDDOWSON, and A. G. MYERS. "ChemInform Abstract: Structure of an anti-Aldol Addition Product of Benzaldehyde and a Pseudoephedrine-Derived O-Silyl Ketene N,O-Acetal." ChemInform 24, no. 9 (2010): no. http://dx.doi.org/10.1002/chin.199309031.

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36

OPPOLZER, W., C. STARKEMANN, I. RODRIGUEZ, and G. BERNARDINELLI. "ChemInform Abstract: Enantiomerically Pure, Crystalline ′Anti′-Aldols from N- Acylbornanesultams Aldolization, and Structure of Intermediate t- Butyldimethylsilyl N,O-Ketene Acetal." ChemInform 22, no. 49 (2010): no. http://dx.doi.org/10.1002/chin.199149061.

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37

Lan, Jin, Zongbo Xie, Jiangnan Yang, Jia Meng, Yishuai Liu, and Zhanggao Le. "One-Pot Multi-component Synthesis of N,O-Acetal Compounds Catalyzed by D-Proline at Room Temperature." Chinese Journal of Organic Chemistry 40, no. 5 (2020): 1331. http://dx.doi.org/10.6023/cjoc201911010.

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38

Jung, Jong-Wha, Dong-Yun Shin, Seung-Yong Seo, et al. "A new entry to functionalized cycloalkylamines: diastereoselective intramolecular amidoalkylation of N,O-acetal TMS ether possessing allylsilane." Tetrahedron Letters 46, no. 4 (2005): 573–75. http://dx.doi.org/10.1016/j.tetlet.2004.11.136.

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39

Suh, Young-Ger, Seok-Ho Kim, Jae-Kyung Jung та Dong-Yun Shin. "The versatile conversion of lactams to the α-alkylated azacycles via cyclic N,O-acetal TMS ether". Tetrahedron Letters 43, № 17 (2002): 3165–67. http://dx.doi.org/10.1016/s0040-4039(02)00459-8.

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40

Sudo, Atsushi, Ryoichi Kudoh, Hiroshi Nakayama, Kazuya Arima, and Takeshi Endo. "Selective Formation of Poly(N,O-acetal) by Polymerization of 1,3-Benzoxazine and Its Main Chain Rearrangement." Macromolecules 41, no. 23 (2008): 9030–34. http://dx.doi.org/10.1021/ma8013178.

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41

Möhrle, Hans, and Heinz Dwuletzki. "Lactam-acetale als potentielle Enamin-Synthone in Heterocyclensynthesen, 2. Das Lactam-acetal/Keten-N,O-acetal-System in der [4 + 2]-Diels-Alder-Reaktion mit inversem Elektronenbedarf." Chemische Berichte 119, no. 12 (1986): 3600–3606. http://dx.doi.org/10.1002/cber.19861191209.

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42

Nakamura, Tatsuya, Kei Kubota, Takanori Ieki, and Seijiro Hosokawa. "Stereoselective Alkylation of the Vinylketene Silyl N,O-Acetal and Its Application to the Synthesis of Mycocerosic Acid." Organic Letters 18, no. 1 (2015): 132–35. http://dx.doi.org/10.1021/acs.orglett.5b03422.

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43

Wang, Xue-Mei, Yi-Wen Liu, Rui-Jun Ma, Chang-Mei Si, and Bang-Guo Wei. "Synthesis of 1,4- and 1,5-Amino Alcohols via Nucleophilic Addition of Semicyclic N,O-Acetal with Organozinc Reagents." Journal of Organic Chemistry 84, no. 17 (2019): 11261–67. http://dx.doi.org/10.1021/acs.joc.9b01545.

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44

Kim, Haejin, Wontaeck Lim, Donghong Im, Dong-gil Kim, and Young Ho Rhee. "Synthetic Strategy for Cyclic Amines: A Stereodefined Cyclic N,O-Acetal as a Stereocontrol and Diversity-Generating Element." Angewandte Chemie International Edition 51, no. 48 (2012): 12055–58. http://dx.doi.org/10.1002/anie.201206967.

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45

Kim, Haejin, Wontaeck Lim, Donghong Im, Dong-gil Kim, and Young Ho Rhee. "Synthetic Strategy for Cyclic Amines: A Stereodefined Cyclic N,O-Acetal as a Stereocontrol and Diversity-Generating Element." Angewandte Chemie 124, no. 48 (2012): 12221–24. http://dx.doi.org/10.1002/ange.201206967.

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46

Gao, Weiwei, Xiaodong Wang, Linbin Yao, et al. "Synthesis of an isomer of lycoplanine A via cascade cyclization to construct the spiro-N,O-acetal moiety." Organic & Biomolecular Chemistry 19, no. 8 (2021): 1748–51. http://dx.doi.org/10.1039/d0ob02399j.

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A 6/10/5/5 tetracyclic isomer of lycoplanine A is synthesized using D–A reaction and cascade cyclization to respectively establish the [9.2.2] pentadecane skeleton and spirocenter, providing sufficient experience to synthesize lycoplanine A.
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47

Kliegel, Wolfgang, Jörg Metge, Steven J. Rettig, and James Trotter. "Novel boron chelate complexes from the reaction of salicylaldehydes, tertiary amines, and diphenylborinic or phenylboronic acid. Crystal and molecular structures of two new types of chelated organoborate salts." Canadian Journal of Chemistry 75, no. 9 (1997): 1203–14. http://dx.doi.org/10.1139/v97-145.

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The one-pot reaction of equimolar amounts of salicylaldehyde, diphenylborinic acid anhydride, and a tertiary amine in the presence of an alkanol (R′OH) led to the addition of R′OH to the aldehyde group and the formation of an O,O-acetal moiety within the chelate anion with the charge balanced by an ammonium cation arising from the tertiary amine. Exchanging the diphenylborinic acid in the three-component reaction system for phenylboronic acid did not give the analogous adduct or chelate but one additional mole equivalent of phenylboronic acid (anhydride) was incorporated, leading to a polycycl
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48

Schaefer, W. P., V. Subramanian, and A. G. Myers. "Structure of an 11-membered cyclic silyl enol ether from condensation of methacrolein and a pseudoephedrine-derived O-silyl ketene N,O-acetal." Acta Crystallographica Section C Crystal Structure Communications 48, no. 11 (1992): 2090–92. http://dx.doi.org/10.1107/s0108270192006851.

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49

Hanaya, Tadashi, Kiyoshi Torigoe, Kazuyuki Soranaka, Horoshi Yamamoto, Yao Qizhengt, and Wolfgang Pfleiderer. "Pteridines CV." Pteridines 6, no. 1 (1995): 1–7. http://dx.doi.org/10.1515/pteridines.1995.6.1.1.

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Summary Treatment of L-biopterin (I) with N,N-dimethyformamide dimethyl- (or diethyl)acetal and then with acetic anhydride in pyridine gave 1',2'-di-O-acetyl-N'-(N,N-dimethylaminomethylene)-L-biopterin (4), which was converted by the Mitsunobu reaction into 3-methyl (5) and 3-p-nitrophenetyl derivatives (7). The protective groups on the side chain diols and N2 of these compounds were selectively cleaved to furnish products 6, 8-10, among which 9 is naturally occurring 3-methyl-L-biopterin and 8 is N',N(3)-protected biopterin, a versatile intermediate for various reactions on the side-chain dio
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50

Sekiya, Shinji, Mao Okumura, Kei Kubota, Tatsuya Nakamura, Daisuke Sekine, and Seijiro Hosokawa. "Remote Asymmetric Bromination Reaction with Vinylketene Silyl N,O-Acetal and Its Application to Total Synthesis of Pellasoren A." Organic Letters 19, no. 9 (2017): 2394–97. http://dx.doi.org/10.1021/acs.orglett.7b00920.

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