Cycloadditions of Nonstabilized 2-Azaallyllithiums with Cycloheptatriene

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3099-3102

  Pearson, William H ^a   Mans, Douglas M ^a   Kampf, Jeff W ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COCAINE; CYCLOHEPTANE DERIVATIVE; DRUG DERIVATIVE; FUSED HETEROCYCLIC RINGS; HETEROCYCLIC COMPOUND; LITHIUM DERIVATIVE; POLYENE;

ARTICLE; CHEMISTRY; ELECTRON; SYNTHESIS;

AZA COMPOUNDS; COCAINE; CYCLOHEPTANES; ELECTRONS; HETEROCYCLIC COMPOUNDS, BRIDGED-RING; LITHIUM COMPOUNDS; POLYENES;

EID: 0037026458     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026423i     Document Type: Article

References (60)

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44. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
45. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
46. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
47. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
48. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
49. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
50. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
51. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
52. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
53. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
54. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
55. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
56. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
57. Recent reviews: (a) Knochel, P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: New York, 1991; Vol. 4, pp 865-911. (b) Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, pp 251-273. (c) Marek, I. J. Chem. Soc., Perkin Trans. 1 1999, 535-544. Selected recent references on the carbolithiation of alkenes: (d) Wei, X.; Taylor, R. J. Angew. Chem., Int. Ed. 2000, 39, 409-412. (e) Norsikian, S.; Baudry, M.; Normant, J. F. Tetrahedron Lett. 2000, 41, 6575-6578. (f) Norsikian, S.; Marek, I.; Normant, J.-F. Tetrahedron Lett. 1997, 38, 7523-7526. (g) Robinson, R. P.; Cronin, B. J.; Jones, B. P. Tetrahedron Lett. 1997, 38, 8479-8482. (h) Krief, A.; Remade, B.; Dumont, W. Synlett 1999, 1142-1144. (i) Hoffmann, R. W.; Koberstein, R.; Harms, K. J. Chem. Soc., Perkin Trans. 2 1999, 183-191. (j) Hoffmann, R. W.; Koberstein, R.; Remade, B.; Krief, A. Chem. Commun. 1997, 2189-2190. The use of nitrogen-substituted organolithiums in carbolithiations is relevant to our work. See: (k) Broka, C. A.; Shen, T. J. Am. Chem. Soc. 1989, 111, 2981-2984. (l) Coldham, I.; Hufton, R.; Rathmell, R. E. Tetrahedron Lett. 1997, 38, 7617-7620. (m) Coldham, I.; Lang-Anderson, M. M. S.; Rathmell, R. E., Snowden, D. J. Tetrahedron Lett. 1997, 38, 7621-7624. (n) Coldham, I.; Fernández, J.-C; Price, K. N.; Snowden, D. J. J. Org. Chem. 2000, 65, 3788-3795.
58. For lithium-ene reactions of allylic organolithiums with alkenes, see the following references and the earlier work cited therein: (a) Dieters, A.; Hoppe, D. Angew. Chem., Int. Ed. 1999, 38, 546-548. (b) Cheng, D.; Zhu, S.; Liu, X.; Norton, S. H.; Cohen, T. J. Am. Chem. Soc. 1999, 121, 10241-10242. (c) Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412-413.
59. For lithium-ene reactions of allylic organolithiums with alkenes, see the following references and the earlier work cited therein: (a) Dieters, A.; Hoppe, D. Angew. Chem., Int. Ed. 1999, 38, 546-548. (b) Cheng, D.; Zhu, S.; Liu, X.; Norton, S. H.; Cohen, T. J. Am. Chem. Soc. 1999, 121, 10241-10242. (c) Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412-413.
60. For lithium-ene reactions of allylic organolithiums with alkenes, see the following references and the earlier work cited therein: (a) Dieters, A.; Hoppe, D. Angew. Chem., Int. Ed. 1999, 38, 546-548. (b) Cheng, D.; Zhu, S.; Liu, X.; Norton, S. H.; Cohen, T. J. Am. Chem. Soc. 1999, 121, 10241-10242. (c) Cheng, D.; Knox, K. R.; Cohen, T. J. Am. Chem. Soc. 2000, 122, 412-413.