Tandem lithium-ene cyclization and thiophenoxide expulsion to produce fused vinylcyclopropanes: First observation of allylic lithium oxyanion- induced reactivity and stereoselectivity in intramolecular carbolithiation

Journal of the American Chemical Society

Volumn 122, Issue 2, 2000, Pages 412-413

  Cheng, Dai ^a   Knox, Kevin R ^a   Cohen, Theodore ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL COMPOUND; CYCLOPROPANE DERIVATIVE; LITHIUM;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; MOLECULAR INTERACTION; NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STEREOCHEMISTRY; TANDEM REPEAT;

EID: 0033970914     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja993325s     Document Type: Article

References (39)

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3. The intermolecular analogue of this tandem alkene carbolithiation/ cyclization requires a more nucleophilic anion and a more active alkene: Cohen, T.; Weisenfeld, R. B.; Gapinski, R. E. J. Org. Chem. 1979, 44, 4744-46. Cohen, T.; Sherbine, J. P.; Mendelson, S. A.; Myers, M. Tetrahedron Lett. 1985, 26, 2965-68. Schaumann, E.; Friese, C.; Spanka, C. Synthesis 1986, 1035-1037. Tanaka, K.; Funaki, I.; Kanemasa, S.; Kobayashi, H.; Tanaka, J.; Tsuge, O. Bull. Chem. Soc. Jpn. 1988, 61, 3957-64. Se analogue: Krief, A.; Barbeaux, P.; Guittet, E. Syntett 1990, 509-10. The single intramolecular case involves selenide displacement. Krief, A.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 417-420.
4. The intermolecular analogue of this tandem alkene carbolithiation/ cyclization requires a more nucleophilic anion and a more active alkene: Cohen, T.; Weisenfeld, R. B.; Gapinski, R. E. J. Org. Chem. 1979, 44, 4744- 46. Cohen, T.; Sherbine, J. P.; Mendelson, S. A.; Myers, M. Tetrahedron Lett. 1985, 26, 2965-68. Schaumann, E.; Friese, C.; Spanka, C. Synthesis 1986, 1035-1037. Tanaka, K.; Funaki, I.; Kanemasa, S.; Kobayashi, H.; Tanaka, J.; Tsuge, O. Bull. Chem. Soc. Jpn. 1988, 61, 3957-64. Se analogue: Krief, A.; Barbeaux, P.; Guittet, E. Syntett 1990, 509-10. The single intramolecular case involves selenide displacement. Krief, A.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 417-420.
5. The intermolecular analogue of this tandem alkene carbolithiation/ cyclization requires a more nucleophilic anion and a more active alkene: Cohen, T.; Weisenfeld, R. B.; Gapinski, R. E. J. Org. Chem. 1979, 44, 4744- 46. Cohen, T.; Sherbine, J. P.; Mendelson, S. A.; Myers, M. Tetrahedron Lett. 1985, 26, 2965-68. Schaumann, E.; Friese, C.; Spanka, C. Synthesis 1986, 1035-1037. Tanaka, K.; Funaki, I.; Kanemasa, S.; Kobayashi, H.; Tanaka, J.; Tsuge, O. Bull. Chem. Soc. Jpn. 1988, 61, 3957-64. Se analogue: Krief, A.; Barbeaux, P.; Guittet, E. Syntett 1990, 509-10. The single intramolecular case involves selenide displacement. Krief, A.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 417-420.
6. The intermolecular analogue of this tandem alkene carbolithiation/ cyclization requires a more nucleophilic anion and a more active alkene: Cohen, T.; Weisenfeld, R. B.; Gapinski, R. E. J. Org. Chem. 1979, 44, 4744- 46. Cohen, T.; Sherbine, J. P.; Mendelson, S. A.; Myers, M. Tetrahedron Lett. 1985, 26, 2965-68. Schaumann, E.; Friese, C.; Spanka, C. Synthesis 1986, 1035-1037. Tanaka, K.; Funaki, I.; Kanemasa, S.; Kobayashi, H.; Tanaka, J.; Tsuge, O. Bull. Chem. Soc. Jpn. 1988, 61, 3957-64. Se analogue: Krief, A.; Barbeaux, P.; Guittet, E. Syntett 1990, 509-10. The single intramolecular case involves selenide displacement. Krief, A.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 417-420.
7. The intermolecular analogue of this tandem alkene carbolithiation/ cyclization requires a more nucleophilic anion and a more active alkene: Cohen, T.; Weisenfeld, R. B.; Gapinski, R. E. J. Org. Chem. 1979, 44, 4744- 46. Cohen, T.; Sherbine, J. P.; Mendelson, S. A.; Myers, M. Tetrahedron Lett. 1985, 26, 2965-68. Schaumann, E.; Friese, C.; Spanka, C. Synthesis 1986, 1035-1037. Tanaka, K.; Funaki, I.; Kanemasa, S.; Kobayashi, H.; Tanaka, J.; Tsuge, O. Bull. Chem. Soc. Jpn. 1988, 61, 3957-64. Se analogue: Krief, A.; Barbeaux, P.; Guittet, E. Syntett 1990, 509-10. The single intramolecular case involves selenide displacement. Krief, A.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 417-420.
8. The intermolecular analogue of this tandem alkene carbolithiation/ cyclization requires a more nucleophilic anion and a more active alkene: Cohen, T.; Weisenfeld, R. B.; Gapinski, R. E. J. Org. Chem. 1979, 44, 4744- 46. Cohen, T.; Sherbine, J. P.; Mendelson, S. A.; Myers, M. Tetrahedron Lett. 1985, 26, 2965-68. Schaumann, E.; Friese, C.; Spanka, C. Synthesis 1986, 1035-1037. Tanaka, K.; Funaki, I.; Kanemasa, S.; Kobayashi, H.; Tanaka, J.; Tsuge, O. Bull. Chem. Soc. Jpn. 1988, 61, 3957-64. Se analogue: Krief, A.; Barbeaux, P.; Guittet, E. Syntett 1990, 509-10. The single intramolecular case involves selenide displacement. Krief, A.; Barbeaux, P. Tetrahedron Lett. 1991, 32, 417-420.
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18. Reductive lithiation, another technique that allows the presence of oxyanionic functions, was used in the first examples of intramolecular oxyanion-facilitated addition of unstabilized organolithiums to alkenes; however, the oxyanionic group was in the vicinity of the carbanion rather than the alkene. Mudryk, B.; Cohen, T. J. Am. Chem. Soc. 1993, 115, 3855- 65. Chen, F.; Mudryk, B.; Cohen, T. Tetrahedron 1994, 50, 12793-12810.
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30. (b) Rearrangement of fused vinylcydopropane systems similar to those prepared in the present paper: Baldwin, J. E.; Burrell, R. C. J. Org. Chem. 1999, 64, 3567-71.
31. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-49 and references therein. Feldman, K. S.; Romanelli, A. L.; Ruckle, J. R. E. J. Org. Chem. 1992, 57, 100-110 and references therein. Jung, M. E.; Rayle, H. L. J. Org. Chem. 1997, 62, 4601- 09.
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35. For a summary of synthetic methods for vinylcyclopropanes, see: Schaumann, E.; Kirschning, A.; Narjes, F. J. Org. Chem. 1991, 56, 717-723 and references 6-10 cited therein. Newer methods of production of fused vinylcyclopropanes based on the transition metal cyclization of enynes: Harvey, D. F.; Lund, K. P.; Neil, D. A. J. Am. Chem. Soc. 1992,114, 8424- 34. Oppolzer, W.; Pimm, A.; Stammen, B.; Hume, W. E. Helv. Chim. Acta 1997, 80, 623-639. Montchamp, J.-L.; Negishi, E.-I. J. Am. Chem. Soc. 1998, 120, 5345-46.
36. For a summary of synthetic methods for vinylcyclopropanes, see: Schaumann, E.; Kirschning, A.; Narjes, F. J. Org. Chem. 1991, 56, 717-723 and references 6-10 cited therein. Newer methods of production of fused vinylcyclopropanes based on the transition metal cyclization of enynes: Harvey, D. F.; Lund, K. P.; Neil, D. A. J. Am. Chem. Soc. 1992,114, 8424-34. Oppolzer, W.; Pimm, A.; Stammen, B.; Hume, W. E. Helv. Chim. Acta 1997, 80, 623-639. Montchamp, J.-L.; Negishi, E.-I. J. Am. Chem. Soc. 1998, 120, 5345-46.
37. For a summary of synthetic methods for vinylcyclopropanes, see: Schaumann, E.; Kirschning, A.; Narjes, F. J. Org. Chem. 1991, 56, 717-723 and references 6-10 cited therein. Newer methods of production of fused vinylcyclopropanes based on the transition metal cyclization of enynes: Harvey, D. F.; Lund, K. P.; Neil, D. A. J. Am. Chem. Soc. 1992,114, 8424- 34. Oppolzer, W.; Pimm, A.; Stammen, B.; Hume, W. E. Helv. Chim. Acta 1997, 80, 623-639. Montchamp, J.-L.; Negishi, E.-I. J. Am. Chem. Soc. 1998, 120, 5345-46.
38. For a summary of synthetic methods for vinylcyclopropanes, see: Schaumann, E.; Kirschning, A.; Narjes, F. J. Org. Chem. 1991, 56, 717-723 and references 6-10 cited therein. Newer methods of production of fused vinylcyclopropanes based on the transition metal cyclization of enynes: Harvey, D. F.; Lund, K. P.; Neil, D. A. J. Am. Chem. Soc. 1992,114, 8424- 34. Oppolzer, W.; Pimm, A.; Stammen, B.; Hume, W. E. Helv. Chim. Acta 1997, 80, 623-639. Montchamp, J.-L.; Negishi, E.-I. J. Am. Chem. Soc. 1998, 120, 5345-46.
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