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7
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For recent papers using oxabicyclic precursors, see: (a) Lautens, M. Synlett 1993, 177. (b) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (e) Shipman, M. Contemp. Org. Synth. 1995, 2(1), 1.
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For recent papers using oxabicyclic precursors, see: (a) Lautens, M. Synlett 1993, 177. (b) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (e) Shipman, M. Contemp. Org. Synth. 1995, 2(1), 1.
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For recent papers using oxabicyclic precursors, see: (a) Lautens, M. Synlett 1993, 177. (b) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (e) Shipman, M. Contemp. Org. Synth. 1995, 2(1), 1.
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For recent papers using oxabicyclic precursors, see: (a) Lautens, M. Synlett 1993, 177. (b) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (e) Shipman, M. Contemp. Org. Synth. 1995, 2(1), 1.
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For recent papers using oxabicyclic precursors, see: (a) Lautens, M. Synlett 1993, 177. (b) Lautens, M. Pure Appl. Chem. 1992, 64, 1873 and references therein. Vogel, P.; Fattori, D.; Gasparini, F.; Le Drian, C. Synlett 1990, 173. Ager, D. J.; East, M. B. Tetrahedron 1993, 49, 5683. (e) Shipman, M. Contemp. Org. Synth. 1995, 2(1), 1.
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For examples of the importance of functionalized cyclohexanes in organic synthesis and the approaches to prepare them, see: (a) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779. (b) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129. Balci, M.; Sutbeyaz, Y.; Secen, H. Tetrahedron 1990, 46, 3715.
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0342360660
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For examples of the importance of functionalized cyclohexanes in organic synthesis and the approaches to prepare them, see: (a) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779. (b) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129. Balci, M.; Sutbeyaz, Y.; Secen, H. Tetrahedron 1990, 46, 3715.
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For examples of the importance of functionalized cyclohexanes in organic synthesis and the approaches to prepare them, see: (a) Ferrier, R. J.; Middleton, S. Chem. Rev. 1993, 93, 2779. (b) Oh, T.; Reilly, M. Org. Prep. Proced. Int. 1994, 26, 129. Balci, M.; Sutbeyaz, Y.; Secen, H. Tetrahedron 1990, 46, 3715.
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85033824935
-
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note
-
(a) The ratio of 5 to 6 varied from 1.4:1 to 1:2.8 even when the same reaction was repeated several times, possibly due to the heterogeneous reaction conditions. (b) Some variation in the ratio of products was also observed for this reaction; see ref 6a.
-
-
-
-
19
-
-
85033820847
-
-
note
-
1H NMR spectra.
-
-
-
-
20
-
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33947335391
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HMPA was shown to be an important solvent in the coupling reaction between π-allylnickel complexes with alkyl halides, see: Corey, E. J.; Semmelhack, M. F. J. Am. Chem. Soc. 1967, 89, 2755.
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-
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85033807842
-
-
note
-
The stereochemistry of 9 and 10 was established by X-ray crystallography of the 3,5-dinitrobenzoic acid and 3-chlorobenzoic acid derivatives, respectively; the stereochemistry of 6 was established using NOE studies following a hydroxyl-directed cyclopropanation; the stereochemistry of 12 and 16 was established by chemical means. See the supporting information for details. The author has deposited atomic coordinates for the derivatives of 9 and 10 with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Cyrstallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.
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23
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85033805262
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Ph.D. Thesis, University of Toronto
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Chiu, P. Ph.D. Thesis, University of Toronto, 1994.
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0000632730
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For mechanistic studies of reductive eliminations in nickel-catalyzed coupling reactions, see: (a) Kurosawa, H.; Ohnishi, H.; Emoto, M.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Organometallics 1990, 9, 3038. (b) Kurosawa, H.; Ohnishi, H.; Emoto, M.; Kawasaki, Y.; Murai, S. J. Am. Chem. Soc. 1988, 110, 6272. (c) Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181. Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466.
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Chatani, N.4
Kawasaki, Y.5
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Ikeda, I.7
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27
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0001657022
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For mechanistic studies of reductive eliminations in nickel-catalyzed coupling reactions, see: (a) Kurosawa, H.; Ohnishi, H.; Emoto, M.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Organometallics 1990, 9, 3038. (b) Kurosawa, H.; Ohnishi, H.; Emoto, M.; Kawasaki, Y.; Murai, S. J. Am. Chem. Soc. 1988, 110, 6272. (c) Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181. Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466.
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0000571631
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For mechanistic studies of reductive eliminations in nickel-catalyzed coupling reactions, see: (a) Kurosawa, H.; Ohnishi, H.; Emoto, M.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Organometallics 1990, 9, 3038. (b) Kurosawa, H.; Ohnishi, H.; Emoto, M.; Kawasaki, Y.; Murai, S. J. Am. Chem. Soc. 1988, 110, 6272. (c) Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181. Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466.
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0000846499
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For mechanistic studies of reductive eliminations in nickel-catalyzed coupling reactions, see: (a) Kurosawa, H.; Ohnishi, H.; Emoto, M.; Chatani, N.; Kawasaki, Y.; Murai, S.; Ikeda, I. Organometallics 1990, 9, 3038. (b) Kurosawa, H.; Ohnishi, H.; Emoto, M.; Kawasaki, Y.; Murai, S. J. Am. Chem. Soc. 1988, 110, 6272. (c) Tatsumi, K.; Nakamura, A.; Komiya, S.; Yamamoto, A.; Yamamoto, T. J. Am. Chem. Soc. 1984, 106, 8181. Komiya, S.; Abe, Y.; Yamamoto, A.; Yamamoto, T. Organometallics 1983, 2, 1466.
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