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For sequential asymmetric hydrogenation, see: Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N. Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. Baba, S. E.; Sartor, K.; Poulin, J.-C.; Kagan, H. B. Bull. Soc. Chim. Fr. 1994, 131, 525. See also ref. 3c.
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0008080527
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See also ref. 3c
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For sequential asymmetric hydrogenation, see: Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N. Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629. Baba, S. E.; Sartor, K.; Poulin, J.-C.; Kagan, H. B. Bull. Soc. Chim. Fr. 1994, 131, 525. See also ref. 3c.
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Lindgren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888. Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091.
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0018238841
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Hydrolysis with a 1 M hydrogen chloride gave a complex mixture. The conditions were reported previously, see: Stork, G.; Takahashi, T.; Kawamoto, I.; Suzuki, T. J. Am. Chem. Soc. 1978, 100, 8272.
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22
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0000754650
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The chiral induction by the rhodium-catalyzed asymmetric hydrogenation of 3, as an analog of β-arylitaconic acid, failed due to the steric hindrance of the alkene moiety of 3; see: Christopfel, W. C.; Vineyard, B. D. J. Am. Chem. Soc. 1979, 101, 4406. Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1989, 30, 735.
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Vineyard, B.D.2
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23
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0001529686
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The chiral induction by the rhodium-catalyzed asymmetric hydrogenation of 3, as an analog of β-arylitaconic acid, failed due to the steric hindrance of the alkene moiety of 3; see: Christopfel, W. C.; Vineyard, B. D. J. Am. Chem. Soc. 1979, 101, 4406. Morimoto, T.; Chiba, M.; Achiwa, K. Tetrahedron Lett. 1989, 30, 735.
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Morimoto, T.1
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24
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33845278799
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3, see: Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922.
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Ohta, T.1
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25
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0037922947
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3, see: Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922.
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Takaya, H.1
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Noyori, R.4
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26
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37049095109
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3, see: Ikariya, T.; Ishii, Y.; Kawano, H.; Arai, T.; Saburi, M.; Yoshikawa, S.; Akutagawa, S. J. Chem. Soc., Chem. Commun. 1985, 922.
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Ikariya, T.1
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Saburi, M.5
Yoshikawa, S.6
Akutagawa, S.7
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27
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84882319392
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2BINAP complex affords only 35% ee; see: Zhang, X.; Uemura, T.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Takaya, H. Synlett 1994, 501.
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Synlett
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Zhang, X.1
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Kumobayashi, H.5
Takaya, H.6
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28
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85087192573
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note
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3, respectively.
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29
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3643104981
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note
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When the reaction was carried out at 60°C, complete lactonization was observed in the product where the keto group was also hydrogenated.
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30
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0025215149
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The absolute configuration was determined by conversion into (2R)-2-benzyl-1,3-propanediol 1-acetate, see: Atsuumi, S.; Nakano, M.; Koike, Y.; Tanaka, S.; Ohkubo, M.; Yonezawa, T.; Funabashi, H.; Hashimoto, J.; Morishima, H. Tetrahedron Lett. 1990, 31, 1601.
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Tetrahedron Lett.
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Atsuumi, S.1
Nakano, M.2
Koike, Y.3
Tanaka, S.4
Ohkubo, M.5
Yonezawa, T.6
Funabashi, H.7
Hashimoto, J.8
Morishima, H.9
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31
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35848945419
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DPPA (diphenyl phosphorazidate). For the modified Curtius reaction, see: Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151. Wittenberger, S. J.; Baker, W. R.; Donner, B. G. Tetrahedron 1993, 49, 1547.
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Tetrahedron
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Ninomiya, K.1
Shioiri, T.2
Yamada, S.3
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32
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0027498907
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DPPA (diphenyl phosphorazidate). For the modified Curtius reaction, see: Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151. Wittenberger, S. J.; Baker, W. R.; Donner, B. G. Tetrahedron 1993, 49, 1547.
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Tetrahedron
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Wittenberger, S.J.1
Baker, W.R.2
Donner, B.G.3
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33
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85087190148
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note
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1H NMR analyses of its diBOC acetate 16.
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