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0028863315
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For a preliminary report see: Kotsuki, H., Hayakawa, H.; Wakao, M.; Shimanouchi, T.; Ochi, M. Tetrahedron: Asymmetry 1993, 6, 2665.
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0001026230
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0000397241
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(b) Kotsuki, H.; Hayashida, K.; Shimanouchi, T.; Nishizawa, H. J. Org. Chem. 1996, 61, 984.
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85082943077
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Epoxides are now readily available in optically pure form via chemical or biological transformations: Pfenninger, A. Synthesis 1986, 89.
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Pfenninger, A.1
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34
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-
37049171559
-
-
Commercially available optically active epoxides were used throughout this work, and all high-pressure reactions were conducted with a Hikari-Koatsu HR-15-B3 apparatus. Bis-epoxide 7 was prepared from D-mannitol according to the literature procedure: Wiggins, L. F. J. Chem. Soc. 1946, 384.
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Wiggins, L.F.1
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0021946141
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0018696775
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0001376141
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LeCloux, D. D.; Tokar, C. J.; Osawa, M.; Houser, R. P.; Keyes, M. C.; Tolman, W. B. Orgarwmetallics 1994, 13, 2855.
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-
41
-
-
85033536797
-
-
It has been known that 4 exists as a mixture of two tautomers in which the N2-H tautomer is the major component.6' All efforts to improve the regioselectivity in this reaction failed.
-
It has been known that 4 exists as a mixture of two tautomers in which the N2-H tautomer is the major component.6' All efforts to improve the regioselectivity in this reaction failed.
-
-
-
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42
-
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84970595437
-
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House, D. A.; Steel, P. J.; Watson, A. A. Aust. J. Chem. 1986, 39, 1525.
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0001667616
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Watson, A. A.; House, D. A.; Steel, P. J. Polyhedron 1989, 8, 1345.
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Watson, A.A.1
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44
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0000102722
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Sobrados, I.3
Elguero, J.4
Meutermans, W.5
-
45
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-
85033529252
-
-
The authors have deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinate can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
-
The authors have deposited atomic coordinates for these structures with the Cambridge Crystallographic Data Centre. The coordinate can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
-
-
-
-
46
-
-
85033531128
-
-
It should be emphasized, however, that this argument is only based on solid-state conformational preferences, which may be quite different in solution.
-
It should be emphasized, however, that this argument is only based on solid-state conformational preferences, which may be quite different in solution.
-
-
-
-
47
-
-
0029882380
-
-
For a similar finding, see: Barz, M.; Herdtweck, E.; Thiel, W. R. Tetrahedron: Asymmetry 1996, 7, 1717.
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Barz, M.1
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4243714728
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Lawrence, D.S.1
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33748502022
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Bernstein, J.; Davis, R. E.; Shimoni, L.; Chang, N.-L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1555.
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Bernstein, J.1
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52
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85033535023
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Wiley: New York, 1973; Collect.
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Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 755.
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Organic Syntheses
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37049082787
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For some recent examples, see: Soai, K.; Niwa, S.; Hori, H. J. Chem. Soc., Chem. Commun. 1990, 982.
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Soai, K.1
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0026673861
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Conti, S.; Falorni, M.; Giacomelli, G.; Soccolini, F. Tetrahedron 1992, 48, 8993.
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Baker, R. W.; Rea, S. O.; Sargent, M. V.; Schenkelaars, E. M. C.; Skelton, B. W.; White, A. H. Tetrahedron: Asymmetry 1994, 5, 45.
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65
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0028217008
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Ishizaki, M.; Fujita, K.; Shimamoto, M.; Hoshino, O. Tetrahedron: Asymmetry 1994, 5, 411.
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Ishizaki, M.1
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Shibata, T.1
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0029059144
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Kotsuki, H.; Nakagawa, Y.; Moriya, N.; Tateishi, H.; Ochi, M.; Suzuki, T.; Isobe, K. Tetrahedron: Asymmetry 1995, 6, 1165.
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Kotsuki, H.1
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70
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0028228802
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See also: Nowotny, S.; Vettel, S.; Knöchel, P. Tetrahedron Lett. 1994, 35, 4539.
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Nowotny, S.1
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0028272208
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and references cited therein.
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74
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85033534245
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PM3-optimized structures of the lowest energy conformations are shown. Calculations were performed by MOPAC '93 implemented in ANCHOR II, a molecular design system for SUN computers, developed by FUJITSU, Ltd., and Kureha Chemical Industry Co., Ltd., 1992. MOPAC 93: Stewart, J. J. P. Fujitsu, Ltd., Tokyo, Japan, 1993.
-
PM3-optimized structures of the lowest energy conformations are shown. Calculations were performed by MOPAC '93 implemented in ANCHOR II, a molecular design system for SUN computers, developed by FUJITSU, Ltd., and Kureha Chemical Industry Co., Ltd., 1992. MOPAC 93: Stewart, J. J. P. Fujitsu, Ltd., Tokyo, Japan, 1993.
-
-
-
-
75
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0026738290
-
-
Unless otherwise noted CDCb was used as the solvent for the NMR experiments.
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For general experimental information, see our previous paper: Kotsuki, H.; Nishikawa, H.; Mon, Y.; Ochi, M. J. Org. Chem. 1992, 57, 5036. Unless otherwise noted CDCb was used as the solvent for the NMR experiments.
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(1992)
J. Org. Chem.
, vol.57
, pp. 5036
-
-
Kotsuki, H.1
Nishikawa, H.2
Mon, Y.3
Ochi, M.4
-
76
-
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85033539679
-
-
Unfortunately, the 13C NMR signals of the pentafluorophenyl ring were too weak to observe.
-
Unfortunately, the 13C NMR signals of the pentafluorophenyl ring were too weak to observe.
-
-
-
-
77
-
-
85033538665
-
-
Interestingly, the cyclohexane carbons were detected to be nonequivalent. Clearly, this may be indicative of an internal hydrogen bonding between hydroxyl and pyrazole nitrogen groups.
-
Interestingly, the cyclohexane carbons were detected to be nonequivalent. Clearly, this may be indicative of an internal hydrogen bonding between hydroxyl and pyrazole nitrogen groups.
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