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1

Frontier, Alison J., Shukree Abdul-Rashed, and Connor Holt. "Alkynyl Prins and Alkynyl Aza-Prins Annulations: Scope and Synthetic Applications." Synthesis 52, no. 14 (2020): 1991–2007. http://dx.doi.org/10.1055/s-0039-1690869.

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This review focuses on alkynyl Prins and alkynyl aza-Prins cyclization­ processes, which involve intramolecular coupling of an alkyne with either an oxocarbenium or iminium electrophile. The oxocarbenium or iminium species can be generated through condensation- or elimination-type processes, to achieve an overall bimolecular annulation that enables the synthesis of both oxygen- and nitrogen-containing­ saturated heterocycles with different ring sizes and substitution patterns. Also discussed are cascade processes in which alkynyl Prins heterocyclic adducts react to trigger subsequent pericycli
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2

Diez-Varga, Alberto, Héctor Barbero, Francisco J. Pulido, Alfonso González-Ortega, and Asunción Barbero. "Competitive Silyl-Prins Cyclization versus Tandem Sakurai-Prins Cyclization: An Interesting Substitution Effect." Chemistry - A European Journal 20, no. 43 (2014): 14112–19. http://dx.doi.org/10.1002/chem.201403421.

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3

Jasti, Ramesh, and Scott D. Rychnovsky. "Racemization in Prins Cyclization Reactions." Journal of the American Chemical Society 128, no. 41 (2006): 13640–48. http://dx.doi.org/10.1021/ja064783l.

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4

Tsui, Gavin Chit, Luping Liu, and Benjamin List. "The Organocatalytic Asymmetric Prins Cyclization." Angewandte Chemie International Edition 54, no. 26 (2015): 7703–6. http://dx.doi.org/10.1002/anie.201500219.

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5

Chen, Chuanfeng, and Patrick S. Mariano. "An Oxidative Prins Cyclization Methodology." Journal of Organic Chemistry 65, no. 10 (2000): 3252–54. http://dx.doi.org/10.1021/jo0000832.

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6

Kobayashi, Naoko, Kazuma Kaneko, Sho Amemiya, Keiichi Noguchi, Masahiro Yamanaka, and Akio Saito. "Alkyne aza-Prins cyclization of N-(hexa-3,5-diynyl)tosylamides with aldehydes using triflic acid and a binuclear aluminum complex." Chemical Communications 55, no. 59 (2019): 8619–22. http://dx.doi.org/10.1039/c9cc03700d.

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The alkyne aza-Prins cyclization of 3,5-diynyl amides and various aldehydes was developed as a first example of the aza-Prins cyclization with the introduction of TfO groups. This method could be applied to homopropargyl amides.
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7

Olier, Clarisse, Mustapha Kaafarani, Stéphane Gastaldi, and Michèle P. Bertrand. "Synthesis of tetrahydropyrans and related heterocycles via prins cyclization; extension to aza-prins cyclization." Tetrahedron 66, no. 2 (2010): 413–45. http://dx.doi.org/10.1016/j.tet.2009.10.069.

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8

Roy, Snigdha. "Prins-Friedel-Crafts Cyclization: Synthesis of Diversely Functionalized Six- Membered Oxacycles." Current Organic Chemistry 25, no. 5 (2021): 635–51. http://dx.doi.org/10.2174/1385272825666210114105020.

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Prins cyclization is a well-established synthetic protocol to generate a wide range of important oxygen heterocycles. It is a cyclization reaction performed by an oxocarbenium ion that undergoes an intramolecular pi-bond attack to construct a new carbon-carbon bond. When this cyclization process is conjugated with Friedel-Crafts reaction, it further expands the synthetic potential by fabricating two different carbon-carbon bonds in one single reaction. Different acid catalysts mediated the coupled Prins-Friedel-Crafts reaction which is conducted both in stepwise as well as in tandem fashion. I
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9

Hazarika, Nabajyoti, Barnali Sarmah, Manobjyoti Bordoloi, Prodeep Phukan, and Gakul Baishya. "Diastereoselective synthesis of tetrahydropyrans via Prins–Ritter and Prins–arylthiolation cyclization reactions." Organic & Biomolecular Chemistry 15, no. 9 (2017): 2003–12. http://dx.doi.org/10.1039/c6ob02692c.

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10

Diez-Varga, Alberto, Hector Barbero, Francisco J. Pulido, Alfonso Gonzalez-Ortega, and Asuncion Barbero. "ChemInform Abstract: Competitive Silyl-Prins Cyclization versus Tandem Sakurai-Prins Cyclization: An Interesting Substitution Effect." ChemInform 46, no. 15 (2015): no. http://dx.doi.org/10.1002/chin.201515246.

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11

Overman, Larry E., and Lewis D. Pennington. "A new strategy for synthesis of attached rings." Canadian Journal of Chemistry 78, no. 6 (2000): 732–38. http://dx.doi.org/10.1139/v00-022.

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The first investigation of the use of pinacol-terminated Prins cyclizations to form attached rings is reported. Treatment of triisopropylsilyl ethers of (Z)- or (E)-[2-(6,6-dimethoxyhexylidene)cyclohexanol with SnCl4 provides bicyclic products having attached rings. The approach is synthetically useful in the Z alkylidenecyclohexane series, proceeding selectively by a pathway involving carbon migration in the pinacol rearrangement step, to provide methoxy epimers of 1-(2-methoxycyclohexyl)cyclopentylcarboxaldehyde. Reaction of the corresponding E stereoisomer is more complex and yields a mixtu
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12

M. Pastor, Isidro, and Miguel Yus. "Focused Update on the Prins Reaction and the Prins Cyclization." Current Organic Chemistry 16, no. 10 (2012): 1277–312. http://dx.doi.org/10.2174/138527212800564196.

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13

Liu, Luping, Philip S. J. Kaib, Aurélien Tap, and Benjamin List. "A General Catalytic Asymmetric Prins Cyclization." Journal of the American Chemical Society 138, no. 34 (2016): 10822–25. http://dx.doi.org/10.1021/jacs.6b07240.

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14

Cao, Ziping, Shan Li, Jie Li та ін. "Gold-catalyzed π-directed regioselective cyclization of bis(o-alkynyl benzyl alcohols): rapid access to dihydroisobenzofuran derivatives". New Journal of Chemistry 40, № 10 (2016): 8211–15. http://dx.doi.org/10.1039/c6nj02066f.

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15

Amemiya, Sho, Shingo Okemoto, Akira Tsubouchi та Akio Saito. "Synthesis of α-(aminoethyl)-α,β-enones via alkyne aza-Prins cyclization and their synthetic application to pyrrolidines". Organic & Biomolecular Chemistry 19, № 13 (2021): 2959–67. http://dx.doi.org/10.1039/d1ob00072a.

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16

Arpin, Patrice, Bryan Hill, Robin Larouche-Gauthier та Claude Spino. "Prins cyclization of α-bromoethers under basic conditions". Canadian Journal of Chemistry 91, № 12 (2013): 1193–201. http://dx.doi.org/10.1139/cjc-2013-0337.

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α-Bromoethers have been found to undergo Prins-type cyclization under basic conditions and without the need to add a promoter. The products are those derived from a Markovnikov addition on the pendant alkene. However, the stereochemistry and even the structure of the products sometimes differ from those expected with the classical Lewis-acid-catalyzed Prins reaction of acetals.
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17

Pastor, Isidro M., and Miguel Yus. "ChemInform Abstract: Focused Update on the Prins Reaction and the Prins Cyclization." ChemInform 43, no. 38 (2012): no. http://dx.doi.org/10.1002/chin.201238244.

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18

Sun, Huai-Ri, Qingyang Zhao, Hui Yang, et al. "Chiral Phosphoric-Acid-Catalyzed Cascade Prins Cyclization." Organic Letters 21, no. 17 (2019): 7143–48. http://dx.doi.org/10.1021/acs.orglett.9b02714.

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19

Metzger, J., U. Biermann, and A. Lützen. "2,3,4,6-Tetrasubstituted Tetrahydropyrans by Prins-Type Cyclization." Synfacts 2006, no. 9 (2006): 0931. http://dx.doi.org/10.1055/s-2006-949236.

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20

Chen, Chuanfeng, and Patrick S. Mariano. "ChemInform Abstract: An Oxidative Prins Cyclization Methodology." ChemInform 31, no. 36 (2010): no. http://dx.doi.org/10.1002/chin.200036144.

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21

Tsui, Gavin Chit, Luping Liu, and Benjamin List. "ChemInform Abstract: The Organocatalytic Asymmetric Prins Cyclization." ChemInform 46, no. 43 (2015): no. http://dx.doi.org/10.1002/chin.201543150.

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22

Yadav, J., B. Reddy, T. Maity, and G. Kumar. "Synthesis of 4-Azidotetrahydropyrans via Prins Cyclization." Synfacts 2008, no. 11 (2008): 1152. http://dx.doi.org/10.1055/s-0028-1083491.

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23

Cho, Yong Seo, Hye Yeon Kim, Joo Hwan Cha, et al. "Indium Trichloride Mediated Intramolecular Prins-Type Cyclization." Organic Letters 4, no. 12 (2002): 2025–28. http://dx.doi.org/10.1021/ol025856i.

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24

Yadav, Jhillu, M. Venkatesh, N. Thrimurtulu, and Attaluri Prasad. "Stereoselective Synthesis of (-)-PF1163A via Prins Cyclization." Synlett 2010, no. 08 (2010): 1255–59. http://dx.doi.org/10.1055/s-0029-1219839.

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25

Tadpetch, Kwanruthai, and Scott D. Rychnovsky. "Rhenium(VII) Catalysis of Prins Cyclization Reactions." Organic Letters 10, no. 21 (2008): 4839–42. http://dx.doi.org/10.1021/ol8019204.

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26

Zheng, Deping, Wanchun Gong, Zuodong Ma, et al. "Unexpected Prins cyclization: iron-promoted cyclization/hydration of alkynyl-dimethyl acetals." Tetrahedron Letters 52, no. 2 (2011): 314–17. http://dx.doi.org/10.1016/j.tetlet.2010.11.035.

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27

Lalli, Claudia, and Pierre van de Weghe. "Enantioselective Prins cyclization: BINOL-derived phosphoric acid and CuCl synergistic catalysis." Chem. Commun. 50, no. 56 (2014): 7495–98. http://dx.doi.org/10.1039/c4cc02826k.

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28

Veeraraghavan Ramachandran, P., and Pravin D. Gagare. "One-pot allyl-/crotylboration-Prins cyclization of aldehydes." Tetrahedron Letters 52, no. 34 (2011): 4378–81. http://dx.doi.org/10.1016/j.tetlet.2011.06.043.

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29

Yadav, J., B. Reddy, D. Chaya, et al. "Synthesis of 4-Iodopiperidines via Aza-Prins Cyclization." Synfacts 2008, no. 7 (2008): 0682. http://dx.doi.org/10.1055/s-2008-1078473.

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30

Han, Xun, GuangRong Peh, and Paul E. Floreancig. "Prins-Type Cyclization Reactions in Natural Product Synthesis." European Journal of Organic Chemistry 2013, no. 7 (2013): 1193–208. http://dx.doi.org/10.1002/ejoc.201201557.

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31

Hirai, Kenji, Rie Takeda, James A. Hutchison, and Hiroshi Uji‐i. "Modulation of Prins Cyclization by Vibrational Strong Coupling." Angewandte Chemie International Edition 59, no. 13 (2020): 5332–35. http://dx.doi.org/10.1002/anie.201915632.

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32

Greco, Sandro Jose, Rodolfo Goetze Fiorot, Valdemar Lacerda, and Reginaldo Bezerra dos Santos. "ChemInform Abstract: Recent Advances in the Prins Cyclization." ChemInform 46, no. 14 (2015): no. http://dx.doi.org/10.1002/chin.201514302.

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33

Zhao, Li-Ming, Fei Dou, Rui Sun, and Ai-Li Zhang. "Regioselective Synthesis of Substituted Tetrahydrofurans through Prins Cyclization." Synlett 25, no. 10 (2014): 1431–34. http://dx.doi.org/10.1055/s-0033-1341273.

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34

Sabitha, Gowravaram, M. Prasad, K. Shankaraiah, and Jhillu Yadav. "Stereoselective Total Synthesis of Obolactone via Prins Cyclization." Synthesis 2010, no. 21 (2010): 3761. http://dx.doi.org/10.1055/s-0030-1258304.

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35

Sabitha, Gowravaram, M. Prasad, K. Shankaraiah, and Jhillu Yadav. "Stereoselective Total Synthesis of Obolactone via Prins Cyclization." Synthesis 2010, no. 07 (2010): 1171–75. http://dx.doi.org/10.1055/s-0029-1219227.

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36

Hirai, Kenji, Rie Takeda, James A. Hutchison, and Hiroshi Uji‐i. "Modulation of Prins Cyclization by Vibrational Strong Coupling." Angewandte Chemie 132, no. 13 (2020): 5370–73. http://dx.doi.org/10.1002/ange.201915632.

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37

Yadav, J. S., B. V. Subba Reddy, D. N. Chaya, and GG KS Narayana Kumar. "Bismuth-triflate-catalyzed Prins–Ritter reaction — An efficient synthesis of 4-amidotetrahydropyrans." Canadian Journal of Chemistry 86, no. 8 (2008): 769–73. http://dx.doi.org/10.1139/v08-080.

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Bismuth(III) triflate is found to be an effective Lewis acid in catalyzing a three-component reaction of homoallylic alcohol, carbonyl compound, and nitrile at ambient temperature via the Prins–Ritter sequence to furnish 4-amidotetrahydropyrans in high yields, all with cis selectivity. Spirocyclic 4-amidotetrahydropyrans are obtained in case of cyclic ketones.Key words: Prins cyclization, bismuth(III) triflate, homoallyl alcohol, 4-amidotetrahydropyrans.
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38

Liu, Yi, and Ying-Yeung Yeung. "Ring strain-dictated divergent fluorinating Prins cyclization or semipinacol rearrangement." Organic & Biomolecular Chemistry 15, no. 31 (2017): 6478–82. http://dx.doi.org/10.1039/c7ob01567d.

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39

Sawant, Rajiv T., Marc Y. Stevens, and Luke R. Odell. "Acetic acid-promoted cascade N-acyliminium ion/aza-Prins cyclization: stereoselective synthesis of functionalized fused tricyclic piperidines." Chemical Communications 53, no. 13 (2017): 2110–13. http://dx.doi.org/10.1039/c6cc09805c.

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A simple, efficient and stereoselective synthesis of novel fused piperidine/3,4-dihydroquinazolinone scaffolds via an imine/cyclization/N-acyliminium ion/aza-Prins cascade reaction sequence is described.
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40

Hinkle, Robert J., Yuzhou Chen, Colleen P. Nofi, and Shane E. Lewis. "Electronic effects on a one-pot aromatization cascade involving alkynyl-Prins cyclization, Friedel–Crafts alkylation and dehydration to tricyclic benzo[f]isochromenes." Organic & Biomolecular Chemistry 15, no. 36 (2017): 7584–93. http://dx.doi.org/10.1039/c7ob01412k.

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A short, efficient cyclization/aromatization cascade affords tricyclic 1,4-dihydro-2H-benzo[f]isochromenes. Electronic factors suggest concerted alkynyl-Prins and Friedel–Crafts reactions in the sequence.
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41

Zheng, Deping, Wanchun Gong, Zuodong Ma, et al. "ChemInform Abstract: Unexpected Prins Cyclization: Iron-Promoted Cyclization/Hydration of Alkynyl-Dimethyl Acetals." ChemInform 42, no. 14 (2011): no. http://dx.doi.org/10.1002/chin.201114066.

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42

Vandavasi, Jaya Kishore, Wan-Ping Hu, Siva Senthil Kumar Boominathan, Bing-Chun Guo, Cheng-Tien Hsiao, and Jeh-Jeng Wang. "Au(i)-catalyzed synthesis of 8-oxabicyclo[3.2.1]oct-2-enes and 9-oxabicyclo[3.3.1]nona-2,6-dienes from enynol via oxonium/Prins-type cyclization." Chemical Communications 51, no. 62 (2015): 12435–38. http://dx.doi.org/10.1039/c5cc02847g.

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43

Rapelli, Chandrashekhar, Balasubramanian Sridhar, and B. V. Subba Reddy. "Correction: Tandem Prins cyclization for the synthesis of indole fused spiro-1,4-diazocane scaffolds." Organic & Biomolecular Chemistry 18, no. 36 (2020): 7224. http://dx.doi.org/10.1039/d0ob90122a.

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Correction for ‘Tandem Prins cyclization for the synthesis of indole fused spiro-1,4-diazocane scaffolds’ by Chandrashekhar Rapelli et al., Org. Biomol. Chem., 2020, 18, 6710–6715, DOI: 10.1039/D0OB01384F.
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44

Zheng, Jie, Shuyu Meng, and Quanrui Wang. "Cascade intramolecular Prins/Friedel–Crafts cyclization for the synthesis of 4-aryltetralin-2-ols and 5-aryltetrahydro-5H-benzo[7]annulen-7-ols." Beilstein Journal of Organic Chemistry 17 (June 22, 2021): 1481–89. http://dx.doi.org/10.3762/bjoc.17.104.

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The treatment of 2-(2-vinylphenyl)acetaldehydes or 3-(2-vinylphenyl)propanals with BF3·Et2O results in an intramolecular Prins reaction affording intermediary benzyl carbenium ions, which are then trapped by a variety of electron-rich aromatics via Friedel–Crafts alkylation. This cascade Prins/Friedel–Crafts cyclization protocol paves an expedient path to medicinally useful 4-aryltetralin-2-ol and 5-aryltetrahydro-5H-benzo[7]annulen-7-ol derivatives.
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45

Miao, Jianzhuang, Yi-Xuan Zheng, Linna Wang, et al. "Toward the total synthesis of grayanane diterpene mollanol A by a Prins [3 + 2] strategy." Organic & Biomolecular Chemistry 18, no. 10 (2020): 1877–80. http://dx.doi.org/10.1039/d0ob00160k.

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A Prins-type [3 + 2] cyclization to form a five-membered ring was developed using an unprotected hydroxyaldehyde and activating-group-free olefins, which efficiently constructed the ADE ring segment of mollanol A.
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46

Saikia, Anil K., Kiran Indukuri, and Jagadish Das. "Stereoselective synthesis of O-tosyl azabicyclic derivatives via aza Prins reaction of endocyclic N-acyliminium ions: application to the total synthesis of (±)-epi-indolizidine 167B and 209D." Org. Biomol. Chem. 12, no. 36 (2014): 7026–35. http://dx.doi.org/10.1039/c4ob01130a.

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A diastereoselective synthesis of 4-O-tosyl piperidine containing azabicyclic derivatives has been established via Prins cyclization reaction. This protocol has been applied for the total synthesis of (±)-epi-indolizidine 167B and 209D.
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47

Reddy, Kachi, Iara Rosa, Antônio Doriguetto, Erick Bastos, and Luiz Silva. "Iodine-Catalyzed Prins Cyclization of Homoallylic Alcohols and Aldehydes." Molecules 18, no. 9 (2013): 11100–11130. http://dx.doi.org/10.3390/molecules180911100.

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48

Chan, Kok-Ping, Yvonne Hui Ling, and Teck-Peng Loh. "Formal synthesis of (+)-SCH 351448: the Prins cyclization approach." Chemical Communications, no. 9 (2007): 939. http://dx.doi.org/10.1039/b616558c.

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49

Jung, Michael E., Steve Angelica, and Derin C. D'Amico. "An Intramolecular Prins Double Cyclization Catalyzed by Silyl Triflates1." Journal of Organic Chemistry 62, no. 26 (1997): 9182–87. http://dx.doi.org/10.1021/jo971337v.

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50

Yadav, J. S., Md Ataur Rahman, N. Mallikarjuna Reddy, and A. R. Prasad. "Synthesis of spiroketal fragment of ossamycin via Prins cyclization." Tetrahedron Letters 56, no. 2 (2015): 365–67. http://dx.doi.org/10.1016/j.tetlet.2014.11.097.

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