Synthesis of 7-azabicyclo[2.2.1]heptanes by anionic cyclization

Tetrahedron Letters

Volumn 40, Issue 9, 1999, Pages 1819-1822

  Coldham, Iain ^a   Fernàndez, Joan Carles ^a   Snowden, David J ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

7 AZABICYCLO[2.2.1]HEPTANE DERIVATIVE; HEPTANE; LITHIUM; TIN; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; ISOMERISM; METAL BINDING; ORGANIC CHEMISTRY; SPECIES DIFFERENCE; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 0033605398     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00018-0     Document Type: Article

References (26)

1. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
2. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
3. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
4. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
5. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
6. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
7. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
8. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
9. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
10. 1. For recent exemples of anionic cyclizations onto alkenes, see Bailey, W.F.; Longstaff, S.C. J. Org. Chem., 1998, 63, 432; Bailey, W.F.; Carson, M.W. J. Org. Chem., 1998, 63, 361; Ahmed, A.; Clayden, J.; Rowley, M. Chem. Commum., 1998, 297; Katritzky, A.R.; Qi, M. Tetrahedron, 1998, 54, 2647; Lorthiois, E.; Marek, I.; Normant, J.F. J. Org. Chem., 1998, 63, 2442; Oestreich, M.; Frölich, R.; Hoppe, D. Tetrahedron Lett., 1998, 39, 1745; Nakamura, E.; Sakata, G.; Kubota, K. Tetrahedron Lett., 1998, 39, 2157; Woltering, M.J., Frölich, R.; Wibbeling, B.; Hoppe, D. Synlett, 1998, 797; Barluenga, J.; Sanz, R.; Granados, A.; Fañanás, F.J. J. Am. Chem. Soc., 1998, 120, 4865; Nishiyama, H.; Sakata, N.; Sugimoto, H.; Motoyama, Y.; Wakita, H.; Nagase, H. Synlett, 1998, 930.
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