Asymmetric cyclization of achiral olefinic organolithiums controlled by a stereogenic lithium intramolecular carbolithiation in the presence of (-)- sparteine [12]

Journal of the American Chemical Society

Volumn 122, Issue 28, 2000, Pages 6787-6788

  Bailey, William F ^a   Mealy, Michael J ^a  

^a UNIVERSITY OF CONNECTICUT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; LITHIUM; ORGANOLITHIUM COMPOUND; SPARTEINE;

CHEMICAL STRUCTURE; CYCLIZATION; LETTER; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0034686683     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000471l     Document Type: Letter

References (36)

1. For a review, see: Bailey, W. F.; Ovaska, T. V. In Advances in Detailed Reaction Mechanisms; Coxon, J. M., Ed.; JAI Press: Greenwich, CT, 1994; Vol. 3, Mechanisms of Importance in Synthesis, pp 251-273.
2. For leading references, see: (a) Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 1999. (b) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 9, 2442. (c) Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788. (d) Bailey, W. F.; Rossi, K. J. Am. Chem. Soc. 1989, 111, 765. (e) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058. (f) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053. (g) Cooke, M. P., Jr. J. Org. Chem. 1992, 57, 1495 and references therein. (h) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (i) Bailey, W. F.; Jiang, X.-L.; McLeod, C. E. J. Org. Chem. 1995, 60, 7791. (j) Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435 and references therein. (k) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
3. For leading references, see: (a) Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 1999. (b) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 9, 2442. (c) Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788. (d) Bailey, W. F.; Rossi, K. J. Am. Chem. Soc. 1989, 111, 765. (e) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058. (f) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053. (g) Cooke, M. P., Jr. J. Org. Chem. 1992, 57, 1495 and references therein. (h) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (i) Bailey, W. F.; Jiang, X.-L.; McLeod, C. E. J. Org. Chem. 1995, 60, 7791. (j) Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435 and references therein. (k) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
4. For leading references, see: (a) Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 1999. (b) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 9, 2442. (c) Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788. (d) Bailey, W. F.; Rossi, K. J. Am. Chem. Soc. 1989, 111, 765. (e) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058. (f) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053. (g) Cooke, M. P., Jr. J. Org. Chem. 1992, 57, 1495 and references therein. (h) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (i) Bailey, W. F.; Jiang, X.-L.; McLeod, C. E. J. Org. Chem. 1995, 60, 7791. (j) Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435 and references therein. (k) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
5. For leading references, see: (a) Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 1999. (b) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 9, 2442. (c) Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788. (d) Bailey, W. F.; Rossi, K. J. Am. Chem. Soc. 1989, 111, 765. (e) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058. (f) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053. (g) Cooke, M. P., Jr. J. Org. Chem. 1992, 57, 1495 and references therein. (h) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (i) Bailey, W. F.; Jiang, X.-L.; McLeod, C. E. J. Org. Chem. 1995, 60, 7791. (j) Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435 and references therein. (k) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
6. For leading references, see: (a) Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 1999. (b) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 9, 2442. (c) Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788. (d) Bailey, W. F.; Rossi, K. J. Am. Chem. Soc. 1989, 111, 765. (e) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058. (f) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053. (g) Cooke, M. P., Jr. J. Org. Chem. 1992, 57, 1495 and references therein. (h) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (i) Bailey, W. F.; Jiang, X.-L.; McLeod, C. E. J. Org. Chem. 1995, 60, 7791. (j) Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435 and references therein. (k) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
7. For leading references, see: (a) Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 1999. (b) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 9, 2442. (c) Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788. (d) Bailey, W. F.; Rossi, K. J. Am. Chem. Soc. 1989, 111, 765. (e) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058. (f) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053. (g) Cooke, M. P., Jr. J. Org. Chem. 1992, 57, 1495 and references therein. (h) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (i) Bailey, W. F.; Jiang, X.-L.; McLeod, C. E. J. Org. Chem. 1995, 60, 7791. (j) Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435 and references therein. (k) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
8. For leading references, see: (a) Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 1999. (b) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 9, 2442. (c) Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788. (d) Bailey, W. F.; Rossi, K. J. Am. Chem. Soc. 1989, 111, 765. (e) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058. (f) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053. (g) Cooke, M. P., Jr. J. Org. Chem. 1992, 57, 1495 and references therein. (h) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (i) Bailey, W. F.; Jiang, X.-L.; McLeod, C. E. J. Org. Chem. 1995, 60, 7791. (j) Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435 and references therein. (k) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
9. For leading references, see: (a) Bailey, W. F.; Patricia, J. J.; DelGobbo, V. C.; Jarret, R. M.; Okarma, P. J. J. Org. Chem. 1985, 50, 1999. (b) Bailey, W. F.; Nurmi, T. T.; Patricia, J. J.; Wang, W. J. Am. Chem. Soc. 1987, 109, 9, 2442. (c) Chamberlin, A. R.; Bloom, S. H.; Cervini, L. A.; Fotsch, C. H. J. Am. Chem. Soc. 1988, 110, 4788. (d) Bailey, W. F.; Rossi, K. J. Am. Chem. Soc. 1989, 111, 765. (e) Bailey, W. F.; Khanolkar, A. D. J. Org. Chem. 1990, 55, 6058. (f) Bailey, W. F.; Khanolkar, A. D.; Gavaskar, K. V. J. Am. Chem. Soc. 1992, 114, 8053. (g) Cooke, M. P., Jr. J. Org. Chem. 1992, 57, 1495 and references therein. (h) Lautens, M.; Kumanovic, S. J. Am. Chem. Soc. 1995, 117, 1954. (i) Bailey, W. F.; Jiang, X.-L.; McLeod, C. E. J. Org. Chem. 1995, 60, 7791. (j) Krief, A.; Kenda, B.; Remacle, B. Tetrahedron 1996, 52, 7435 and references therein. (k) Coldham, I.; Hufton, R.; Snowden, D. J. J. Am. Chem. Soc. 1996, 118, 5322.
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