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1
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84920342971
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New address: Institut für Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin
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New address: Institut für Chemie, Freie Universität Berlin, Takustr. 3, 14195 Berlin
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2
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0032912089
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c) R. J. Sundberg in Comprehensive Heterocyclic Chemistry II (Eds. A. R. Katritzky, C. W. Rees, E. F. V. Scriven), p. 119-206, Pergamon: Oxford 1996.
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b) A. Merz, J. Kronberger, L. Dunsch, A. Neudeck, A. Petr, L. Parkanyi, Angew. Chem. 1999, 111, 1533-1538; Angew. Chem. Int. Ed. 1999, 38, 1442-1446 and references cited.
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0345650495
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in press
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For a recent review see: H.-U. Reissig, S. Hormuth, W. Schade, M. Okala Amombo, T. Watanabe, R. Pulz, A. Hausherr, R. Zimmer, J. Heterocyclic Chem. 2000, in press.
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For general reviews on the reactivity of alkoxyallenes see: a) R. Zimmer, Synthesis 1993, 165-178.
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Zimmer, R.1
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Initial work: a) S. Hoff, L. Brandsma, J. F. Arens, Recl. Trav. Chim. Pays-Bas 1968, 87, 1179-1184.
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Recl. Trav. Chim. Pays-Bas
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Hoff, S.1
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Arens, J.F.3
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84977283958
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For applications to asymmetric syntheses
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b) S. Hoff, L. Brandsma, J. F. Arens, Recl. Trav. Chim. Pays-Bas 1969, 88, 609-619. For applications to asymmetric syntheses:
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Recl. Trav. Chim. Pays-Bas
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Hoff, S.1
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e) S. Hormuth, H.-U. Reissig, D. Dorsch, Angew. Chem. 1993, 105, 1513-1514; Angew. Chem. Int. Ed. Engl. 1993, 32, 1449-1450.
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b) L. Brandsma, V. Yu. Vvedensky, N. A. Nedolya, O. A. Tarasova, B. A. Trofimov, Tetrahedron Lett. 1998, 39, 2433-2436.
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25
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0344356018
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Diplomarbeit, Technische Universität Dresden
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M. Okala Amombo, Diplomarbeit, Technische Universität Dresden 1997.
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Okala Amombo, M.1
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2842513604
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a) R. Albrecht, G. Kresze, B. Mlakar, Chem. Ber. 1964, 97, 483-489.
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31
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84920360464
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note
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3S (329.4) Calcd. C 65.63, H 5.81, N 4.25, S 9.73; found C 65.73, H 5.89, N 4.27, S 9.48.
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32
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0000587665
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J. Yoshimura, Y. Ohgo, T. Sato, J. Am. Chem, Soc. 1964, 86, 3858-3862. Also see: L. Battistini, F. Zanardi, G. Rassu, P. Spanu, G. Pelosi, G. G. Fava, M. B. Ferrari, G. Casiraghi, Tetrahedron: Asymmetry 1997, 8, 2975-2987.
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Yoshimura, J.1
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33
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0030828305
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J. Yoshimura, Y. Ohgo, T. Sato, J. Am. Chem, Soc. 1964, 86, 3858-3862. Also see: L. Battistini, F. Zanardi, G. Rassu, P. Spanu, G. Pelosi, G. G. Fava, M. B. Ferrari, G. Casiraghi, Tetrahedron: Asymmetry 1997, 8, 2975-2987.
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Tetrahedron: Asymmetry
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Battistini, L.1
Zanardi, F.2
Rassu, G.3
Spanu, P.4
Pelosi, G.5
Fava, G.G.6
Ferrari, M.B.7
Casiraghi, G.8
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34
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84920343679
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note
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Primary adducts with an N-alkyl substituent such as 22 seem to undergo faster cyclization to 2,5-dihydropyrrole derivatives.
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35
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0001271879
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Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann, Thieme, Stuttgart
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For additions of organometallic reagents to this imine see: ref. 15. For general reviews on stereoselective additions to imines see: a) N. Risch, M. Arend in Stereoselective Synthesis of Organic Compounds/Methods of Organic Chemistry (Houben-Weyl), 4th Ed., Vol. E21b (Eds.: G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann), Thieme, Stuttgart 1995, p. 1833-2010.
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Stereoselective Synthesis of Organic Compounds/Methods of Organic Chemistry (Houben-Weyl), 4th Ed.
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c) R. Bloch, Chem. Rev. 1998, 98, 1407-1438.
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Chem. Rev.
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Bloch, R.1
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38
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0345650489
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unpublished results, Technische Universität Dresden
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A 1,2-oxazine with syn-configuration could be converted into 23. T. Watanabe, unpublished results, Technische Universität Dresden 1998.
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Watanabe, T.1
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39
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0345650490
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unpublished results, Technische Universität Dresden
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A. Hausherr, unpublished results, Technische Universität Dresden 1999.
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Hausherr, A.1
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0001919984
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Performed in analogy to L. Brandsma, H. D. Verkruijsse, W. Verboom, P. E. Van Riju, J. Organomet. Chem. 1982, 232, C1-C4.
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41
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84920361755
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note
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The cyclization of 25 is probably stereospecific. Thus, diastereomer 25a provides only cis-substituted 28a whereas the slower reacting 25b gives trans-isomer 28b. Details will be presented in a full paper.
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42
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0023740316
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For related 5-endo-trig cyclizations of allenyl amines furnishing 2,5-dihydropyrrole derivatives see: a) J. S. Prasad, L. S. Liebeskind, Tetrahedron Lett. 1988, 29, 4253-4256.
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Tetrahedron Lett.
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Prasad, J.S.1
Liebeskind, L.S.2
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Ohno, M.1
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Yamaoka, Y.6
Fujii, N.7
Ibuka, T.8
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