Synthesis of (±)-kainic acid by dearomatising cyclisation of a lithiated N-benzyl p-anisamide

Chemical Communications

Volumn , Issue 4, 2000, Pages 317-318

  Clayden, Jonathan ^a   Tchabanenko, Kirill ^a  

^a UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

KAINIC ACID;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034696110     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909325g     Document Type: Article

References (46)

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2. Dearomatising anionic cyclisations are also known in the naphthamide series: A. Ahmed, J. Clayden and M. Rowley, Chem. Commun., 1998, 297; A. Ahmed, J. Clayden and M. Rowley, Tetrahedron Lett., 1998, 39, 6103; R. A. Bragg and J. Clayden, Tetrahedron Lett., 1999, 40, 8323; Tetrahedron Lett., 1999, 40, 8327. There are reports of similar reactions of aryl sulfones: J. K. Crandall andT. A. Ayers, J. Org. Chem., 1992, 57, 2993; A. Padwa, M. A. Filipkowski, D. N. Kline, S. S. Murphree and P. E. Yeske, J. Org. Chem., 1993, 58, 2061.
3. Dearomatising anionic cyclisations are also known in the naphthamide series: A. Ahmed, J. Clayden and M. Rowley, Chem. Commun., 1998, 297; A. Ahmed, J. Clayden and M. Rowley, Tetrahedron Lett., 1998, 39, 6103; R. A. Bragg and J. Clayden, Tetrahedron Lett., 1999, 40, 8323; Tetrahedron Lett., 1999, 40, 8327. There are reports of similar reactions of aryl sulfones: J. K. Crandall andT. A. Ayers, J. Org. Chem., 1992, 57, 2993; A. Padwa, M. A. Filipkowski, D. N. Kline, S. S. Murphree and P. E. Yeske, J. Org. Chem., 1993, 58, 2061.
4. Dearomatising anionic cyclisations are also known in the naphthamide series: A. Ahmed, J. Clayden and M. Rowley, Chem. Commun., 1998, 297; A. Ahmed, J. Clayden and M. Rowley, Tetrahedron Lett., 1998, 39, 6103; R. A. Bragg and J. Clayden, Tetrahedron Lett., 1999, 40, 8323; Tetrahedron Lett., 1999, 40, 8327. There are reports of similar reactions of aryl sulfones: J. K. Crandall andT. A. Ayers, J. Org. Chem., 1992, 57, 2993; A. Padwa, M. A. Filipkowski, D. N. Kline, S. S. Murphree and P. E. Yeske, J. Org. Chem., 1993, 58, 2061.
5. Dearomatising anionic cyclisations are also known in the naphthamide series: A. Ahmed, J. Clayden and M. Rowley, Chem. Commun., 1998, 297; A. Ahmed, J. Clayden and M. Rowley, Tetrahedron Lett., 1998, 39, 6103; R. A. Bragg and J. Clayden, Tetrahedron Lett., 1999, 40, 8323; Tetrahedron Lett., 1999, 40, 8327. There are reports of similar reactions of aryl sulfones: J. K. Crandall andT. A. Ayers, J. Org. Chem., 1992, 57, 2993; A. Padwa, M. A. Filipkowski, D. N. Kline, S. S. Murphree and P. E. Yeske, J. Org. Chem., 1993, 58, 2061.
6. Dearomatising anionic cyclisations are also known in the naphthamide series: A. Ahmed, J. Clayden and M. Rowley, Chem. Commun., 1998, 297; A. Ahmed, J. Clayden and M. Rowley, Tetrahedron Lett., 1998, 39, 6103; R. A. Bragg and J. Clayden, Tetrahedron Lett., 1999, 40, 8323; Tetrahedron Lett., 1999, 40, 8327. There are reports of similar reactions of aryl sulfones: J. K. Crandall andT. A. Ayers, J. Org. Chem., 1992, 57, 2993; A. Padwa, M. A. Filipkowski, D. N. Kline, S. S. Murphree and P. E. Yeske, J. Org. Chem., 1993, 58, 2061.
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