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1
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0036482040
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Kusano G., Orihara S., Tsukamoto D., Shibano M., Coskun M., Guvenc A., and Erdurak C.S. Chem. Pharm. Bull. 50 (2002) 185-192
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Kusano, G.1
Orihara, S.2
Tsukamoto, D.3
Shibano, M.4
Coskun, M.5
Guvenc, A.6
Erdurak, C.S.7
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8
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33846910659
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note
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1H NMR signals.
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-
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12
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0007278761
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and references cited therein
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Cohen L.A., and Witkop B. Angew. Chem. 73 (1979) 253-276 and references cited therein
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(1979)
Angew. Chem.
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Cohen, L.A.1
Witkop, B.2
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13
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33846920030
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2, see e.g.:
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16
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0000620801
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Saitoh Y., Moriyama Y., Hirota H., Takahashi T., and Khuong-Huu Q. Bull. Chem. Soc. 54 (1981) 488-492
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Saitoh, Y.1
Moriyama, Y.2
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Khuong-Huu, Q.5
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20
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0003793022
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Solvomercuration/Demercuration Reactions in Organic Synthesis, Chapter VII
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Springer, Berlin and references cited therein
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Larock R.C. Solvomercuration/Demercuration Reactions in Organic Synthesis, Chapter VII. Amidomercuration (1986), Springer, Berlin 505-521 and references cited therein
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(1986)
Amidomercuration
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Larock, R.C.1
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22
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33846909174
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For N→π-cyclization with iodine, see:
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-
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26
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33846894896
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For N→π-cyclization with benzeneselenyl chloride, see:
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-
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29
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33846908440
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For Bronsted-acids catalysed N→π-cyclization, see:
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33
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33846936426
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note
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These compounds were synthesized by the same reaction sequence as 6 starting with the α-alkylation of β-hydroxyester 3 with 1-bromo-hex-2-ene and 1-bromo-undec-2-ene, respectively. Hydrazinolysis followed by Curtius rearrangement and N→π-cyclization with mercury(II) acetate gave the bicyclic compounds in 67% and 69% yields over four steps, respectively.
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34
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33846901068
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note
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Alkylation experiments with bromide 9 also afforded β-oxoester 11 but only in poor yields (20%). Therefore bromide 9 was converted to the more reactive iodide 10.
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-
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36
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33846895113
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For further examples of alkylations of β-keto ester dianions, see:
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-
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38
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0028076364
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Angle S.R., Arnaiz D.O., Boyce J.P., Frutos R.P., Louie M.S., Mattson-Arnaiz H.L., Rainier J.D., Turnbull K.D., and Yang W. J. Org. Chem. 5 (1994) 6322-6337
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(1994)
J. Org. Chem.
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Angle, S.R.1
Arnaiz, D.O.2
Boyce, J.P.3
Frutos, R.P.4
Louie, M.S.5
Mattson-Arnaiz, H.L.6
Rainier, J.D.7
Turnbull, K.D.8
Yang, W.9
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45
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33846895854
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For enantioselective reduction of β-keto esters with BINAP-Ru(II) complexes, also see:
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46
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33845282793
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Noyori R., Ohkuma T., Kitamura M., Takaya H., Sayo N., Kumobayashi H., and Akutagawa S. J. Am. Chem. Soc. 109 (1987) 5856-5858
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(1987)
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Noyori, R.1
Ohkuma, T.2
Kitamura, M.3
Takaya, H.4
Sayo, N.5
Kumobayashi, H.6
Akutagawa, S.7
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47
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33845278216
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Kitamura M., Ohkuma T., Inoue S., Sayo N., Kumobayashi H., Akutagawa S., Ohta T., Takaya H., and Noyori R. J. Am. Chem. Soc. 110 (1988) 629-631
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(1988)
J. Am. Chem. Soc.
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Kitamura, M.1
Ohkuma, T.2
Inoue, S.3
Sayo, N.4
Kumobayashi, H.5
Akutagawa, S.6
Ohta, T.7
Takaya, H.8
Noyori, R.9
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52
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0000676432
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Mashima K., Kusano K., Sato N., Matsumura Y., Nozaki K., Kumobayashi H., Sayo Y., Hori Y., Ishizaki T., Akutagawa S., and Takaya H. J. Org. Chem. 59 (1994) 3064-3076
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(1994)
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Mashima, K.1
Kusano, K.2
Sato, N.3
Matsumura, Y.4
Nozaki, K.5
Kumobayashi, H.6
Sayo, Y.7
Hori, Y.8
Ishizaki, T.9
Akutagawa, S.10
Takaya, H.11
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54
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33846924232
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note
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®.
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55
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33846925460
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note
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1H NMR signals.
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56
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33846931032
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note
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According to Ref. 1 pharmacological activity regarding α-glucosidase inhibition could not be observed so far.
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