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7
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8
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(b) Ko, B.-T.; Wu, C.-C.; Lin, C.-C. Organometallics 2000, 19, 1864.
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Ko, B.-T.1
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9
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(c) Konishi, K.; Makita, K.; Aida, T.; Inoue, S. J. Chem. Soc., Chem. Commun. 1988, 643.
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10
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(d) Ooi, T.; Miura, T.; Maruoka, K. Angew Chem., Int. Ed. 1998, 37, 2347.
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(e) Campbell, E. J.; Zhou, H.; Nguyen, S. T. Org. Lett. 2001, 3, 2391.
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Campbell, E.J.1
Zhou, H.2
Nguyen, S.T.3
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12
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30744447423
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note
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The MPV reduction was generally not considered In give good diastereaselectivities. See ref 2u.
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13
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33750111587
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(a) Lund, H. Ber, 1937, 70B, 1520.
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(1937)
Ber
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Lund, H.1
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14
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37049176898
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(b) Jackman, L. M.; Macbeth, A. K.; Mills, J. A. J. Chem. Soc. 1949, 1949, 2641.
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J. Chem. Soc.
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Jackman, L.M.1
Macbeth, A.K.2
Mills, J.A.3
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16
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0013215651
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(d) Mueller, H. K.; Sehuat, J.; Baborowski, H. J. Prakt. Chem. 1973, 315, 1045.
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Mueller, H.K.1
Sehuat, J.2
Baborowski, H.3
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19
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30744478621
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EP 703209, 1996
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(g) Hilpert, H. EP 703209, 1996.
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Hilpert, H.1
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25
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30744479147
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(b) Anakabe, E.; Badin, D.; Carrillo, L.; Rodrigues, M.; Vicario, J. L. Trends Org. Chem. 2001, 9, 29.
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Anakabe, E.1
Badin, D.2
Carrillo, L.3
Rodrigues, M.4
Vicario, J.L.5
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26
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0004139082
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Krieger: Malabar, FL
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Enantiomers, Racemates, and Resolutions; Jacques, J., Collet. A., Wilen, S. H., Eds.; Krieger: Malabar, FL, 1991.
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Enantiomers, Racemates, and Resolutions
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Jacques, J.1
Collet, A.2
Wilen, S.H.3
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32
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0026600147
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(a) Skiles, J. W.; Fuchs, V.; Miao, C.; Sorcek, R.; Grozinger, K. G.; Maukldin, S. C.; Vitous, J.; Mui, P. W.; Jacober, S.; Chow, G.; Matteo, M.; Skoog, M.; Weklon, S. M.; Possanza, G.; Keirns, J.; Letts, G.; Rosenthn, A. S. J. Med. Chem. 1992, 35, 641.
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Skiles, J.W.1
Fuchs, V.2
Miao, C.3
Sorcek, R.4
Grozinger, K.G.5
Maukldin, S.C.6
Vitous, J.7
Mui, P.W.8
Jacober, S.9
Chow, G.10
Matteo, M.11
Skoog, M.12
Weklon, S.M.13
Possanza, G.14
Keirns, J.15
Letts, G.16
Rosenthn, A.S.17
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33
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30744435556
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(b) Kami, S.; Yokomatsu, T.; Iwasawa, H.; Shibuya, S. Tetrahedron Lett. 1987, 28, 0331.
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Tetrahedron Lett.
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Kami, S.1
Yokomatsu, T.2
Iwasawa, H.3
Shibuya, S.4
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34
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30744434595
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note
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Unlike many other ketones in Table 2, the product isomers 3a/5a are readily separated by LC for easy analysis during screening.
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35
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0000144758
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Iguchi, S.; Nakai, H.; Hayashi, M.; Yamamoto, H. J. Org. Chem. 1979, 44, 1363. BHT = 2,6-di-tert-butyl-4-methylphenol.
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J. Org. Chem.
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Iguchi, S.1
Nakai, H.2
Hayashi, M.3
Yamamoto, H.4
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36
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30744454766
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note
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N-H of the carbamate on 2n provides the third equiv of a proton to fully quench DIBAL's two isobutyl groups and one hydride.
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37
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33947300580
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3 without IPA was very sluggish, It has been proposed that IPA can help convert the tetramer of aluminum isopropoxide to the much more reactive form (∼2.8 oligomer). Shiner, V. J.; Whiltaker, D. J. Am. Chem. Sac. 1969, 91, 394.
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J. Am. Chem. Sac.
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, pp. 394
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Shiner, V.J.1
Whiltaker, D.2
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38
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30744446914
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note
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3, suggesting the deactivation of the catalyst to a less active form during the reaction.
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39
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30744467892
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note
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It was found that addition of a catalytic amount of bipyridine resulted in a slower MPV reduction.
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40
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0028935576
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(a) Bisacchi, G. S.; Ahmad, S.; Alam, M.; Ashfaq, A.; Barrish, J.; Cheng, P. T. W.; Greytok, J.; Hermsmier, M.; Lin, P. F.; Merchant, Z.; Skoog, M.; Spergal, S.; Zahler, R. Bioorg. Med. Chem. Lett. 1995, 5, 459.
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Bioorg. Med. Chem. Lett.
, vol.5
, pp. 459
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Bisacchi, G.S.1
Ahmad, S.2
Alam, M.3
Ashfaq, A.4
Barrish, J.5
Cheng, P.T.W.6
Greytok, J.7
Hermsmier, M.8
Lin, P.F.9
Merchant, Z.10
Skoog, M.11
Spergal, S.12
Zahler, R.13
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42
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30744466112
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note
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We also observed about the same d.r. at 3 h (∼60% conv) as that at 18 h for the MPV reduction of 2a.
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43
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0028246815
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A moderate d.r. (8/9 ∼2;1) has been reported using other methods: (a) Burk, M. J.; Harper, T. G. P.; Lee, J. R.; Karberg, C. Tetrahedron Lett. 1994, 35, 4963.
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(1994)
Tetrahedron Lett.
, vol.35
, pp. 4963
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Burk, M.J.1
Harper, T.G.P.2
Lee, J.R.3
Karberg, C.4
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44
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0001675801
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(b) Shibata, I.; Yoshida, T.; Kawakami, T.; Baba, A.; Matsuda, H. J. Org. Chem. 1992, 57, 4049.
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J. Org. Chem.
, vol.57
, pp. 4049
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Shibata, I.1
Yoshida, T.2
Kawakami, T.3
Baba, A.4
Matsuda, H.5
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45
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0000192115
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Most other reducing agents also gave high anti/syn ratios: (a) Davis, F. A.; Haque, M. S.; Przeslawski, R. M. J. Org. Chem. 1989, 54, 2021.
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(1989)
J. Org. Chem.
, vol.54
, pp. 2021
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Davis, F.A.1
Haque, M.S.2
Przeslawski, R.M.3
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46
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0032473819
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(b) Miyai, T.; Inoue, K.; Yasuda, M.; Shibata, I.; Baba, A. Tetrahedron Lett. 1998, 39, 1929.
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(1998)
Tetrahedron Lett.
, vol.39
, pp. 1929
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Miyai, T.1
Inoue, K.2
Yasuda, M.3
Shibata, I.4
Baba, A.5
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47
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0034706346
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(c) Abernethy, C. D.; Cole, M. L.; Davies, A. J.; Jones, C. Tetrahedron Lett. 2000, 41, 7567.
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(2000)
Tetrahedron Lett.
, vol.41
, pp. 7567
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Abernethy, C.D.1
Cole, M.L.2
Davies, A.J.3
Jones, C.4
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48
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0037154749
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Hoffman, R. C.; Maslouh, N.; Cervantes-Lee, F. J. Org. Chem. 2002, 67, 1045.
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(2002)
J. Org. Chem.
, vol.67
, pp. 1045
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Hoffman, R.C.1
Maslouh, N.2
Cervantes-Lee, F.3
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49
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30744435295
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note
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4 gave an anti/syn selectivity of 94:6.
-
-
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50
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30744451125
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note
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Direct MPV reduction on 2-(ethylamino)propiophenone hydrochloride to give 19/20 was unsuccessful possibly because of the reaction between the amino group and the ketone.
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