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Volumn 61, Issue 21, 1996, Pages 7246-7247

Nickel-catalyzed addition of grignard reagents to oxabicyclic compounds. Ring-opening reactions with previously unreactive substrates and nucleophiles

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EID: 0001598049     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961615a     Document Type: Article
Times cited : (52)

References (29)
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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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    • and references therein
    • 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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    • 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.
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    • note
    • 1H NMR spectra.
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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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    • 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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    • 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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    • 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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    • 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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    • 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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