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(a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer, Berlin, 1999.
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Unmodified ketones as donors: (a) Yamada, Y. M. A.; Yoshikawa, N.; Sasai, H.; Shibasaki, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1871.
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Yoshikawa, N.1
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Das, J.3
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(e) Suzuki, T.; Yamagiwa, N.; Matsuo, Y.; Sakamoto, S.; Yamaguchi, K.; Shibasaki, M.; Noyori, R. Tetrahedron Lett. 2001, 42, 4669.
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Suzuki, T.1
Yamagiwa, N.2
Matsuo, Y.3
Sakamoto, S.4
Yamaguchi, K.5
Shibasaki, M.6
Noyori, R.7
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0034801857
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Unmodified α-hydroxyketones as donors: (f) Yoshikawa, N.; Kumagai, N.; Matsunaga, S.; Moll, G.; Ohshima, T.; Suzuki, T.; Shibasaki, M. J. Am. Chem. Soc. 2001, 123, 2466.
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Yoshikawa, N.1
Kumagai, N.2
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Moll, G.4
Ohshima, T.5
Suzuki, T.6
Shibasaki, M.7
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(g) Kumagai, N.; Matsunaga, S.; Yoshikawa, N.; Ohshima, T.; Shibasaki, M. Org. Lett. 2001, 3, 1539.
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Org. Lett.
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Kumagai, N.1
Matsunaga, S.2
Yoshikawa, N.3
Ohshima, T.4
Shibasaki, M.5
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0034654216
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Unmodified ketones as donors: (a) List, B.; Lerner, R. A.; Barbas, C. F., III. J. Am. Chem. Soc. 2000, 122, 2395.
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List, B.1
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Barbas C.F. III3
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(c) List, B.; Pojarliev, P.; Castello, C. Org. Lett. 2001, 3, 573.
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List, B.1
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(d) Sakthivel, K.; Notz, W.; Bui, T.; Barbas, C. F., III. J. Am. Chem. Soc. 2001, 123, 5260.
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J. Am. Chem. Soc.
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Sakthivel, K.1
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Bui, T.3
Barbas C.F. III4
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16
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0035833675
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(e) Trost, B. M.; Silcoff, E. R.; Ito, H. Org. Lett. 2001, 3, 2497.
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Org. Lett.
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Trost, B.M.1
Silcoff, E.R.2
Ito, H.3
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19
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0034596299
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Unmodified α-hydroxyketones as donors: (h) The use of α-hydroxyketones with chemical catalysts has been pioneered by List et al.: Notz, W.; List, B. J. Am. Chem. Soc. 2000, 122, 7386.
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Notz, W.1
List, B.2
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0034823456
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See, also ref 4d
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(i) Trost, B. M.; Ito, H.; Silcoff, E. R. J. Am. Chem. Soc. 2001, 123, 3367. See, also ref 4d.
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J. Am. Chem. Soc.
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Trost, B.M.1
Ito, H.2
Silcoff, E.R.3
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0034678591
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Review for biological and chemical methods: (a) Machajewski, T. D.; Wong, C.-H. Angew. Chem., Int. Ed. 2000, 39, 1352.
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Angew. Chem., Int. Ed.
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Machajewski, T.D.1
Wong, C.-H.2
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22
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0034604430
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and references therein
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For the use of catalytic antibodies, see: (b) Turner, J. M.; Bui, T.; Lerner, R. A.; Barbas, C. F., III; List, B. Chem Eur. J. 2000, 6, 2772 and references therein.
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Chem Eur. J.
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Turner, J.M.1
Bui, T.2
Lerner, R.A.3
Barbas C.F. III4
List, B.5
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(b) Betancort, J. M.; Sakthivel, K.; Thayumanavan, R.; Barbas, C. F., III. Tetrahedron Lett. 2001, 42, 4441.
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Tetrahedron Lett.
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(c) List, B.; Pojarliev, P.; Martin, H. J. Org. Lett. 2001, 3, 2423.
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Org. Lett.
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List, B.1
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Martin, H.J.3
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For recent reviews on the catalytic asymmetric 1,4-addition reactions, see: (a) Krause, N.; Hoffmann-Röder, A. Synthesis, 2001, 171.
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Synthesis
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Krause, N.1
Hoffmann-Röder, A.2
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30
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0002436782
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Excellent catalytic asymmetric 1,4-addition reactions with latent enolates, such as enol silyl ether, are established (>90% ee), although those reactions require stoichiometric amounts of reagents to prepare latent enolates. For recent representative examples, see: (a) Kobayashi, S.; Suda, S.; Yamada, M.; Mukaiyama, T. Chem Lett. 1994, 97.
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Chem Lett.
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Kobayashi, S.1
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(b) Kitajima, H.; Ito, K.; Katsuki, T. Tetrahedron 1997, 53, 17015.
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Tetrahedron
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(c) Evans, D. A.; Rovis, T.; Kozlowski, M. C.; Downey, W.; Tedrow, J. S. J. Am. Chem. Soc. 2000, 122, 9134.
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Evans, D.A.1
Rovis, T.2
Kozlowski, M.C.3
Downey, W.4
Tedrow, J.S.5
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34
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0034817259
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and references therein
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(e) Evans, D. A.; Scheldt, K. A.; Johnston, J. N.; Willis, M. C. J. Am. Chem. Soc. 2001, 123, 4480 and references therein.
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J. Am. Chem. Soc.
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Evans, D.A.1
Scheldt, K.A.2
Johnston, J.N.3
Willis, M.C.4
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35
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0343967492
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For leading references on catalytic asymmetric 1,4-addition reactions of other carbon nucleophiles, see malonates: (f) Yamaguchi, M.; Shiraishi, T.; Hirama, M. J. Org. Chem. 1996, 61, 3520.
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J. Org. Chem.
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Yamaguchi, M.1
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36
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β-Keto esters: (g) Ji, J.; Barnes, D. M.; Zhang, J.; King, S. A.; Wittenberger, S. J.; Morton, H. E. J. Am. Chem. Soc. 1999, 121, 10215.
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Morton, H.E.6
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α-Cyano esters: (h) Sawamura, M.; Hamashima, H.; Ito, Y. Tetrahedron 1994, 50, 4439.
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Tetrahedron
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Sawamura, M.1
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Ito, Y.3
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39
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0034975355
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See also, ref 8, 10b and references therein
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B reagents: (j) Hayashi, T. Synlett 2001, 879. See also, ref 8, 10b and references therein.
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Synlett
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Hayashi, T.1
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40
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0034654056
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For catalytic asymmetric syntheses using linked-BINOL as a chiral ligand, see: (a) Matsunaga, S.; Das, J.; Roels, J.; Vogl, E. M.; Yamamoto, N.; Iida, T.; Yamaguchi, K.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 2252.
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J. Am. Chem. Soc.
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Matsunaga, S.1
Das, J.2
Roels, J.3
Vogl, E.M.4
Yamamoto, N.5
Iida, T.6
Yamaguchi, K.7
Shibasaki, M.8
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41
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0001392528
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(b) Kim, Y. S.; Matsunaga, S.; Das, J.; Sekine, A.; Ohshima, T.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 6506.
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J. Am. Chem. Soc.
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Kim, Y.S.1
Matsunaga, S.2
Das, J.3
Sekine, A.4
Ohshima, T.5
Shibasaki, M.6
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0034727313
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(c) Matsunaga, S.; Ohshima, T.; Shibasaki, M. Tetrahedron Lett. 2000, 41, 8473.
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Tetrahedron Lett.
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Matsunaga, S.1
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Shibasaki, M.3
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44
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0041718598
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note
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For other chiral bimetallic Zn catalysts, see refs 4b, 4e, 4i and references therein.
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45
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0001148133
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3OH. (a) Moriarty, R. M.; Hu, H.; Gupta, S. C. Tetrahedron Lett. 1981, 22, 1283.
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Tetrahedron Lett.
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Moriarty, R.M.1
Hu, H.2
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0032745171
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(b) Togo, H.; Abe, S.; Noaami, G.; Yokoyama, M. Bull. Chem. Soc. Jpn. 1999, 72, 2351.
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Bull. Chem. Soc. Jpn.
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Togo, H.1
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Yokoyama, M.4
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48
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0041718595
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note
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4. The solvent was removed under reduced pressure, and the residue was purified by flash silica gel column chromatography (hexane/acetone 6/1) to afford 4a (272.5 mg. 0.829 mmol, 83%).
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49
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0035114355
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Hauser, F. M.; Zhou, M.; Sun, Y. Synth. Commun. 2001, 31, 77.
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Synth. Commun.
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Hauser, F.M.1
Zhou, M.2
Sun, Y.3
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50
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0041718596
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See Supporting Information
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See Supporting Information.
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51
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33947085552
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The absolute configurations of 4c and 6a were determined by Mosher's method. Those of others were temporarily determined by analogy, (a) Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
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J. Am. Chem. Soc.
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Dale, J.A.1
Mosher, H.S.2
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52
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0043221179
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note
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The chelate complex formation through the coordination of 2′-methoxy group was essential to achieve high ee in the direct aldol reaction of 2 and aldehydes. See ref 3h.
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53
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0041718597
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note
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The benzoate 7c was prepared by treating 4c with benzoyl chloride. See Supporting Information.
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54
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0015742305
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Tamura, Y.; Fujiwara, H.; Sumoto, K.; Ikeda, M.; Kita, Y. Synthesis 1973, 215.
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Synthesis
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Tamura, Y.1
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Kita, Y.5
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0035944511
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(a) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. C. J. Am. Chem. Soc. 2001, 123, 10409.
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0035819577
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(b) Porter, J. R.; Traverse, J. F.; Hoveyda, A. H.; Snapper, M. C. J. Am. Chem. Soc. 2001, 123, 984.
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Hoveyda, A.H.3
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0034734313
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and references therein
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(c) Ishitani, H.; Ueno, M.; Kobayashi, S. J. Am. Chem. Soc. 2000, 122, 8180 and references therein.
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J. Am. Chem. Soc.
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Ishitani, H.1
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58
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0042218882
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note
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1H NMR analysis of isolated product.
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