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1

Jacobsen, E. Jon, Jeremy Levin, and Larry E. Overman. "Synthesis applications of cationic aza-Cope rearrangements. Part 18. Scope and mechanism of tandem cationic aza-Cope rearrangement-Mannich cyclization reactions." Journal of the American Chemical Society 110, no. 13 (1988): 4329–36. http://dx.doi.org/10.1021/ja00221a037.

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2

Stas, Sara, Kourosch Abbaspour Tehrani, and Georges Laus. "Carbon–carbon bond formation via a tandem cationic 2-aza-Cope rearrangement–Lewis acid promoted Petasis reaction." Tetrahedron 64, no. 16 (2008): 3457–63. http://dx.doi.org/10.1016/j.tet.2008.02.025.

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3

Aron, Zachary D., and Larry E. Overman. "Stereocontrolled Synthesis of Angularly Substituted 1-Azabicyclic Rings by Cationic 2-Aza-Cope Rearrangements." Organic Letters 7, no. 5 (2005): 913–16. http://dx.doi.org/10.1021/ol047330z.

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4

Brummond, Kay M., and Sang-phyo Hong. "A Formal Total Synthesis of (−)-FR901483, Using a Tandem Cationic Aza-Cope Rearrangement/Mannich Cyclization Approach." Journal of Organic Chemistry 70, no. 3 (2005): 907–16. http://dx.doi.org/10.1021/jo0483567.

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5

Cooke, Andrew, Jonathan Bennett, and Emma McDaid. "A facile synthesis of N -benzyl-4-acetylproline via a tandem cationic aza-Cope rearrangement-Mannich reaction." Tetrahedron Letters 43, no. 5 (2002): 903–5. http://dx.doi.org/10.1016/s0040-4039(01)02287-0.

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6

Overman, Larry E., and Soji Sugai. "Total Synthesis of (?)-Crinine. Use of Tandem Cationic Aza-Cope Rearrangement/Mannich Cyclizations for the Synthesis of Enantiomerically PureAmaryllidaceae Alkaloids." Helvetica Chimica Acta 68, no. 3 (1985): 745–49. http://dx.doi.org/10.1002/hlca.19850680324.

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7

OVERMAN, L. E., and J. SHIM. "ChemInform Abstract: Synthesis Applications of Cationic Aza-Cope Rearrangement. Part 24. First Total Synthesis of Amaryllidaceae Alkaloids of the 5,11- Methanomorphanthridine Type. An Efficient Total Synthesis of (.+-.)- Pancracine (I)." ChemInform 23, no. 3 (2010): no. http://dx.doi.org/10.1002/chin.199203253.

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8

Wu, Pei Lin, and Frank W. Fowler. "The 1-aza-Cope rearrangement. 2." Journal of Organic Chemistry 53, no. 26 (1988): 5998–6005. http://dx.doi.org/10.1021/jo00261a003.

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9

Kobayashi, S., M. Sugiura, and C. Mori. "Synthesis of Homoallylic Amines via 2-Aza-Cope Rearrangement." Synfacts 2006, no. 10 (2006): 1061. http://dx.doi.org/10.1055/s-2006-949377.

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10

Agami, Claude, François Couty, Jing Lin, Axelle Mikaeloff та Michel Poursoulis. "Asymmetric synthesis of α-amino acids via cationic aza-cope rearrangements". Tetrahedron 49, № 33 (1993): 7239–50. http://dx.doi.org/10.1016/s0040-4020(01)87201-x.

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11

Merino, Pedro, Tomás Tejero, and Vanni Mannucci. "Experimental and theoretical evidences of 2-aza-Cope rearrangement of nitrones." Tetrahedron Letters 48, no. 19 (2007): 3385–88. http://dx.doi.org/10.1016/j.tetlet.2007.03.071.

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12

Knight, Steven D., Larry E. Overman, and Garry Pairaudeau. "Synthesis applications of cationic aza-Cope rearrangements. 26. Enantioselective total synthesis of (-)-strychnine." Journal of the American Chemical Society 115, no. 20 (1993): 9293–94. http://dx.doi.org/10.1021/ja00073a057.

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13

AGAMI, C., F. COUTY, J. LIN, A. MIKAELOFF та M. POURSOULIS. "ChemInform Abstract: Asymmetric Synthesis of α-Amino Acids via Cationic Aza-Cope Rearrangements." ChemInform 24, № 50 (2010): no. http://dx.doi.org/10.1002/chin.199350286.

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14

Overman, Larry E., Graeme M. Robertson, and Albert J. Robichaud. "Synthesis applications of cationic aza-Cope rearrangements. 20. Total synthesis of (.+-.)-meloscine and (.+-.)-epimeloscine." Journal of Organic Chemistry 54, no. 6 (1989): 1236–38. http://dx.doi.org/10.1021/jo00267a003.

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15

Kawashima, Takayuki, Tsutomu Kihara, and Naoki Inamoto. "The Azaphospha-Cope Rearrangement of 2-Aza-3-phospha-1,5-hexadiene Derivatives." Chemistry Letters 17, no. 4 (1988): 577–80. http://dx.doi.org/10.1246/cl.1988.577.

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16

Zahedi, Ehsan, Safa Ali-Asgari, and Vahid Keley. "NBO and NICS analysis of the allylic rearrangements (the Cope and 3-aza-Cope rearrangements) of hexa-1,5-diene and N-vinylprop-2-en-1-amine: A DFT study." Open Chemistry 8, no. 5 (2010): 1097–104. http://dx.doi.org/10.2478/s11532-010-0084-1.

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AbstractIn this work, ab initio density functional theory (DFT) calculations have been performed on the 3,3-sigmatropic rearrangements of hexa-1,5-diene (Cope) and N-vinylprop-2-en-1-amine (3-aza-Cope) in the gas phase. The barrier heights and heats of reactions calculated at the B3LYP/6-311G** level of theory were in good agreement with experimental data. Transition states optimized with B3LYP/6-311G** theory were used for calculating the nucleus independent chemical shift (NICS) and, a natural bond orbital (NBO) analysis was also performed at the same level of theory. Our results indicate th
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17

Gadde, Karthik, Jonas Daelemans, Bert U. W. Maes та Kourosch Abbaspour Tehrani. "Lewis acidic FeCl3 promoted 2-aza-Cope rearrangement to afford α-substituted homoallylamines in dimethyl carbonate". RSC Advances 9, № 31 (2019): 18013–17. http://dx.doi.org/10.1039/c9ra03277k.

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The current work shows an iron-catalyzed 2-aza-Cope rearrangement in dimethyl carbonate for the synthesis of a wide variety of α-substituted homoallylamines from readily accessible starting materials with diverse functional groups.
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18

Gadde, Karthik, Bert U. W. Maes та Kourosch Abbaspour Tehrani. "HFIP-mediated 2-aza-Cope rearrangement: metal-free synthesis of α-substituted homoallylamines at ambient temperature". Organic & Biomolecular Chemistry 19, № 18 (2021): 4067–75. http://dx.doi.org/10.1039/d1ob00404b.

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A synthesis of α-substituted homoallylamine derivatives is presented, involving the in situ generation of aldimines from readily available aldehydes and 1,1-diphenylhomoallylamines, followed by a 2-aza-Cope rearrangement in HFIP at room temperature.
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19

Hastings, Courtney J., Dorothea Fiedler, Robert G. Bergman, and Kenneth N. Raymond. "Aza Cope Rearrangement of Propargyl Enammonium Cations Catalyzed By a Self-Assembled “Nanozyme”." Journal of the American Chemical Society 130, no. 33 (2008): 10977–83. http://dx.doi.org/10.1021/ja8013055.

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20

Sun, Xi-Shang, Xing-Heng Wang, Hai-Yan Tao, Liang Wei та Chun-Jiang Wang. "Catalytic asymmetric synthesis of quaternary trifluoromethyl α- to ε-amino acid derivatives via umpolung allylation/2-aza-Cope rearrangement". Chemical Science 11, № 40 (2020): 10984–90. http://dx.doi.org/10.1039/d0sc04685j.

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In this study, we developed an efficient Ir-catalyzed cascade umpolung allylation/2-aza-Cope rearrangement for the preparation of a variety of quaternary trifluoromethyl α-ε-amino acids in high yields with excellent enantioselectivities.
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21

Sugiura, Masaharu, Chieko Mori, Keiichi Hirano та Shū Kobayashi. "Direct synthesis of unprotected α-amino acids via allylation of hydroxyglycine". Canadian Journal of Chemistry 83, № 6-7 (2005): 937–42. http://dx.doi.org/10.1139/v05-096.

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Hydroxyglycine, the ammonia adduct of glyoxylic acid, was found to react with various allylboronates in the presence of triethylamine in methanol to give unprotected α-amino acids directly with high stereoselectivity. For instance, the reactions with (E)- and (Z)-crotylboronates afforded the corresponding anti- and syn-crotylated products (isoleucine and alloisoleucine after hydrogenation) with high diastereoselectivity, respectively. Interestingly, it was found that isomerization of the products (γ-adducts to α-adducts) occurred under the reaction conditions in some cases. Control experiments
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22

KNIGHT, S. D., L. E. OVERMAN, and G. PAIRAUDEAU. "ChemInform Abstract: Applications of Cationic Aza-Cope Rearrangements. Part 26. Enantioselective Total Synthesis of (-)-Strychnine." ChemInform 25, no. 4 (2010): no. http://dx.doi.org/10.1002/chin.199404253.

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23

Goodman, C. Guy, та Jeffrey S. Johnson. "Asymmetric Synthesis of β-Amino Amides by Catalytic Enantioconvergent 2-Aza-Cope Rearrangement". Journal of the American Chemical Society 137, № 46 (2015): 14574–77. http://dx.doi.org/10.1021/jacs.5b09593.

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24

KATRITZKY, A. R., D. FENG, M. QI, H. LANG, and P. J. STEEL. "ChemInform Abstract: Synthesis of 3-Alkylideneindolin-2-ones via 3-Aza-Cope Rearrangement." ChemInform 29, no. 11 (2010): no. http://dx.doi.org/10.1002/chin.199811131.

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25

Angle, Steven R., John M. Fevig, Steven D. Knight, Robert W. Marquis, and Larry E. Overman. "Synthesis applications of cationic aza-Cope rearrangements. 24. The aza-Cope-Mannich approach to Strychnos alkaloids. Short stereocontrolled total syntheses of (.+-.)-dehydrotubifoline and (.+-.)-akuammicine." Journal of the American Chemical Society 115, no. 10 (1993): 3966–76. http://dx.doi.org/10.1021/ja00063a016.

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26

Doedens, Robert J., Guy P. Meier, and Larry E. Overman. "Synthesis applications of cationic aza-Cope rearrangements. Part 17. Transition-state geometry of [3,3]-sigmatropic rearrangements of iminium ions." Journal of Organic Chemistry 53, no. 3 (1988): 685–90. http://dx.doi.org/10.1021/jo00238a039.

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27

Tsuda, Masato, Taiki Morita, Shintaro Fukuhara, and Hiroyuki Nakamura. "Synthesis of 4-amino-5-allenylisoxazoles via gold(i)-catalysed propargyl aza-Claisen rearrangement." Organic & Biomolecular Chemistry 19, no. 6 (2021): 1358–64. http://dx.doi.org/10.1039/d0ob02544e.

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28

Overman, Larry E., Mark E. Okazaki, and E. Jon Jacobsen. "Synthesis applications of cationic aza-Cope rearrangements. 16. Stereocontrolled synthesis of substituted cis-cyclopenta[b]pyrrolidines." Journal of Organic Chemistry 50, no. 13 (1985): 2403–5. http://dx.doi.org/10.1021/jo00213a049.

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29

Overman, Larry E., and Steven R. Angle. "Synthesis applications of cationic aza-Cope rearrangements. Stereocontrolled synthesis of hexahydro-1H-pyrrolo[2,3-d]carbazoles." Journal of Organic Chemistry 50, no. 21 (1985): 4021–28. http://dx.doi.org/10.1021/jo00221a012.

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30

ANGLE, S. R., J. M. FEVIG, S. D. KNIGHT, R. W. JUN MARQUIS, and L. E. OVERMAN. "ChemInform Abstract: Synthesis Applications of Cationic Aza-Cope Rearrangements. Part 24. Aza-Cope-Mannich Approach to Strychnos Alkaloids. Short Stereocontrolled Total Syntheses of (.+-.)-Dehydrotubifoline and (.+-.) -Akuammicine." ChemInform 24, no. 40 (2010): no. http://dx.doi.org/10.1002/chin.199340279.

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31

Lukowski, Mark, Kathryn Jacobs, Powen Hsueh, Harriet A. Lindsay, and M. C. Milletti. "Thermodynamic and kinetic factors in the aza-Cope rearrangement of a series of iminium cations." Tetrahedron 65, no. 50 (2009): 10311–16. http://dx.doi.org/10.1016/j.tet.2009.10.010.

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32

Denmark, Scott, and Hyung Chi. "Synthesis of 2-Alkenyl-Tethered Anilines." Synthesis 49, no. 13 (2017): 2873–88. http://dx.doi.org/10.1055/s-0036-1589002.

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Three general routes for the synthesis of (E)-2-alkenyl-tethered anilines have been developed. The first route involves a 3-aza-Cope rearrangement of N-allylic anilines in the presence of a Lewis acid. The requisite N-allylic anilines were prepared by the addition of vinylmagnesium reagents to the corresponding aldimines. The second route details a direct cross-metathesis of 2-allylic or 2-homoallylic anilines with styrenes. The third route involves a palladium-catalyzed C–N cross-coupling of aryl halides. Taken together, these three strategies allowed access to the requisite aniline substrate
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33

Merino, Pedro, Maria Chiacchio, Laura Legnani та Tomás Tejero. "BET & ELF Quantum Topological Analysis of Neutral 2-Aza-Cope Rearrangement of γ-Alkenyl Nitrones". Molecules 22, № 8 (2017): 1371. http://dx.doi.org/10.3390/molecules22081371.

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34

Wang, Ruo‐Qing, Chong Shen, Xiang Cheng, et al. "Sequential Ir‐Catalyzed Allylation/ 2‐aza‐Cope Rearrangement Strategy for the Construction of Chiral Homoallylic Amines †." Chinese Journal of Chemistry 38, no. 8 (2020): 807–11. http://dx.doi.org/10.1002/cjoc.202000065.

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35

Shen, Chong, Ruo-Qing Wang, Liang Wei, Zuo-Fei Wang, Hai-Yan Tao та Chun-Jiang Wang. "Catalytic Asymmetric Umpolung Allylation/2-Aza-Cope Rearrangement for the Construction of α-Tetrasubstituted α-Trifluoromethyl Homoallylic Amines". Organic Letters 21, № 17 (2019): 6940–45. http://dx.doi.org/10.1021/acs.orglett.9b02543.

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36

Lee, Hyun Seung, Sangku Lee, Se Hee Kim, and Jae Nyoung Kim. "Direct one-pot introduction of 2-methylpyridines to Baylis–Hillman adducts via base-mediated 3-aza-Cope rearrangement." Tetrahedron Letters 52, no. 39 (2011): 5039–42. http://dx.doi.org/10.1016/j.tetlet.2011.07.101.

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37

FEVIG, J. M., R. W. JUN MARQUIS, and L. E. OVERMAN. "ChemInform Abstract: Synthesis Applications of Cationic Aza-Cope Rearrangements. Part 22. New Approach to Strychnos Alkaloids. Stereocontrolled Total Synthesis of (.+-.)-Dehydrotubifoline." ChemInform 22, no. 41 (2010): no. http://dx.doi.org/10.1002/chin.199141239.

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38

Shi, Li-Min, Xi-Shang Sun, Chong Shen, Zuo-Fei Wang, Hai-Yan Tao та Chun-Jiang Wang. "Catalytic Asymmetric Synthesis of α-Trifluoromethyl Homoallylic Amines via Umpolung Allylation/2-Aza-Cope Rearrangement: Stereoselectivity and Mechanistic Insight". Organic Letters 21, № 12 (2019): 4842–48. http://dx.doi.org/10.1021/acs.orglett.9b01738.

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39

Lee, Hyun Seung, Sangku Lee, Se Hee Kim, and Jae Nyoung Kim. "ChemInform Abstract: Direct One-Pot Introduction of 2-Methylpyridines to Baylis-Hillman Adducts via Base-Mediated 3-Aza-Cope Rearrangement." ChemInform 43, no. 2 (2011): no. http://dx.doi.org/10.1002/chin.201202156.

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40

Obrecht, Daniel, Cornelia Zumbrunn та Klaus Müller. "Formal [3 + 2] Cycloaddition Reaction of [1,4]Oxazin-2-ones and α-Alkynyl Ketones via a Tandem Mukaiyama-Aldol Addition/Aza-Cope Rearrangement". Journal of Organic Chemistry 64, № 18 (1999): 6891–95. http://dx.doi.org/10.1021/jo9902695.

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41

Jin, Ming, Shi-fu Yin та Shang-Dong Yang. "Bismuth(III)-Catalyzed Sequential Enamine–Imine Tautomerism/2-Aza-Cope Rearrangement of Stable β-Enaminophosphonates: One-Pot Synthesis of β-Aminophosphonates". Organic Letters 22, № 7 (2020): 2811–15. http://dx.doi.org/10.1021/acs.orglett.0c00796.

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42

Niu, Dawen, Liqiang Wan, Lan Tian, and Jie Liu. "Iridium-Catalyzed Asymmetric Umpolung Allylation of N-Fluor­enyl Imines to Prepare 1,4-Disubstituted Homoallylic Amines." Synlett 28, no. 16 (2017): 2051–56. http://dx.doi.org/10.1055/s-0036-1588514.

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The discovery and development of an Ir-catalyzed asymmetric umpolung allylation of imines is discussed here. This method produces 1,4-disubstituted homoallylic amines, a class of compounds that are difficult to access by conventional methods. This reaction proceeds through a sequence involving an allylation and a 2-aza-Cope rearrangement event. The unique mechanistic feature of this reaction could be the reason for its broad substrate scope. The products of this reaction are useful intermediates for various bioactive and natural products. Besides its immediate synthetic utility, we expect this
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43

KNIGHT, S. D., L. E. OVERMAN, and G. PAIRAUDEAU. "ChemInform Abstract: Synthesis Applications of Cationic Aza-Cope Rearrangements. Part 28. Asymmetric Total Syntheses of (-)- and (+)-Strychnine (IX) and the Wieland-Gumlich Aldehyde (VII)." ChemInform 26, no. 38 (2010): no. http://dx.doi.org/10.1002/chin.199538266.

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44

Kuang, Jinqiang, Shaista Parveen, and Bernhard Breit. "Rhodium-Catalyzed Regioselective Domino Azlactone-Alkyne Coupling/Aza-Cope Rearrangement: Facile Access to 2-Allyl-3-oxazolin-5-ones and Trisubstituted Pyridines." Angewandte Chemie International Edition 56, no. 29 (2017): 8422–25. http://dx.doi.org/10.1002/anie.201704022.

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45

Wei, Liang, Lu Xiao, Zuo‐Fei Wang, Hai‐Yan Tao, and Chun‐Jiang Wang. "Ir/Phase‐Transfer‐Catalysis Cooperatively Catalyzed Asymmetric Cascade Allylation/2‐aza‐Cope Rearrangement: An Efficient Route to Homoallylic Amines from Aldimine Esters †." Chinese Journal of Chemistry 38, no. 1 (2019): 82–86. http://dx.doi.org/10.1002/cjoc.201900391.

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46

Kuang, Jinqiang, Shaista Parveen, and Bernhard Breit. "Rhodium-Catalyzed Regioselective Domino Azlactone-Alkyne Coupling/Aza-Cope Rearrangement: Facile Access to 2-Allyl-3-oxazolin-5-ones and Trisubstituted Pyridines." Angewandte Chemie 129, no. 29 (2017): 8542–45. http://dx.doi.org/10.1002/ange.201704022.

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47

Obrecht, Daniel, Cornelia Zumbrunn та Klaus Mueller. "ChemInform Abstract: Formal [3 + 2] Cycloaddition Reaction of [1,4]Oxazin-2-ones and α-Alkynyl Ketones via a Tandem Mukaiyama-Aldol Addition/ Aza-Cope Rearrangement." ChemInform 31, № 3 (2010): no. http://dx.doi.org/10.1002/chin.200003156.

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48

Chen, Xiaobei, Huaqiang Fan, Shilei Zhang, Chenguang Yu, and Wei Wang. "Facile Installation of 2-Reverse Prenyl Functionality into Indoles by a Tandem N-Alkylation-Aza-Cope Rearrangement Reaction and Its Application in Synthesis." Chemistry - A European Journal 22, no. 2 (2015): 716–23. http://dx.doi.org/10.1002/chem.201503355.

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49

Overman, Larry E., and Jaechul Shim. "Synthesis applications of cationic aza-Cope rearrangements. Part 25. Total synthesis of Amaryllidaceae alkaloids of the 5,11-methanomorphanthridine type. Efficient total syntheses of (-)-pancracine and (.+-.)-pancracine." Journal of Organic Chemistry 58, no. 17 (1993): 4662–72. http://dx.doi.org/10.1021/jo00069a032.

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50

Overman, Larry E., and Jaechul Shim. "Synthesis applications of cationic aza-Cope rearrangements. 23. First total synthesis of amaryllidaceae alkaloids of the 5,11-methano morphanthridine type. An efficient total synthesis of (.+-.)-pancracine." Journal of Organic Chemistry 56, no. 17 (1991): 5005–7. http://dx.doi.org/10.1021/jo00017a002.

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