Synthesis of bicyclic lactams via ring closing olefin metathesis and intramolecular Heck reaction

Synlett

Volumn , Issue 3, 2000, Pages 319-322

  Lennartz, Michael ^a   Steckhan, Eberhard ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

Cyclizations; Electrooxidation; Heck reaction; Lactams; Metathesis

Indexed keywords

ALKENE DERIVATIVE; LACTAM DERIVATIVE;

ALKYLATION; ARTICLE; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; REACTION ANALYSIS; SYNTHESIS;

EID: 0034050041     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (23)

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10. For recent reviews, see: Schuster, S., Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. Grubbs, R.H., Miller, S.J., Fu, G. Acc. Chem. Res. 1995, 28, 446. Synthesis of Ncontaining heterocycles using RCM, see: Martin, S.F., Chen, H.J., Courtney, A.K., Liao, Y.S., Patzel, M., Ramser, M.N., Wagman, A.S. Tetrahedron 1996, 52, 7251; Pandit, U.K., Overkleeft, H.S., Borer, B.C., Bieräugel, H. Eur. J. Org. Chem. 1999, 959. Grossmith, C.E., Senia, F., Wagner, J. Synlett 1999, 1660. Diedrichs, N., Westermann, B. Synlett 1999, 1127. Beal, L.M., Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639.
11. For recent reviews, see: Schuster, S., Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. Grubbs, R.H., Miller, S.J., Fu, G. Acc. Chem. Res. 1995, 28, 446. Synthesis of Ncontaining heterocycles using RCM, see: Martin, S.F., Chen, H.J., Courtney, A.K., Liao, Y.S., Patzel, M., Ramser, M.N., Wagman, A.S. Tetrahedron 1996, 52, 7251; Pandit, U.K., Overkleeft, H.S., Borer, B.C., Bieräugel, H. Eur. J. Org. Chem. 1999, 959. Grossmith, C.E., Senia, F., Wagner, J. Synlett 1999, 1660. Diedrichs, N., Westermann, B. Synlett 1999, 1127. Beal, L.M., Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639.
12. For recent reviews, see: Schuster, S., Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. Grubbs, R.H., Miller, S.J., Fu, G. Acc. Chem. Res. 1995, 28, 446. Synthesis of Ncontaining heterocycles using RCM, see: Martin, S.F., Chen, H.J., Courtney, A.K., Liao, Y.S., Patzel, M., Ramser, M.N., Wagman, A.S. Tetrahedron 1996, 52, 7251; Pandit, U.K., Overkleeft, H.S., Borer, B.C., Bieräugel, H. Eur. J. Org. Chem. 1999, 959. Grossmith, C.E., Senia, F., Wagner, J. Synlett 1999, 1660. Diedrichs, N., Westermann, B. Synlett 1999, 1127. Beal, L.M., Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639.
13. For recent reviews, see: Schuster, S., Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. Grubbs, R.H., Miller, S.J., Fu, G. Acc. Chem. Res. 1995, 28, 446. Synthesis of Ncontaining heterocycles using RCM, see: Martin, S.F., Chen, H.J., Courtney, A.K., Liao, Y.S., Patzel, M., Ramser, M.N., Wagman, A.S. Tetrahedron 1996, 52, 7251; Pandit, U.K., Overkleeft, H.S., Borer, B.C., Bieräugel, H. Eur. J. Org. Chem. 1999, 959. Grossmith, C.E., Senia, F., Wagner, J. Synlett 1999, 1660. Diedrichs, N., Westermann, B. Synlett 1999, 1127. Beal, L.M., Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639.
14. For recent reviews, see: Schuster, S., Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. Grubbs, R.H., Miller, S.J., Fu, G. Acc. Chem. Res. 1995, 28, 446. Synthesis of Ncontaining heterocycles using RCM, see: Martin, S.F., Chen, H.J., Courtney, A.K., Liao, Y.S., Patzel, M., Ramser, M.N., Wagman, A.S. Tetrahedron 1996, 52, 7251; Pandit, U.K., Overkleeft, H.S., Borer, B.C., Bieräugel, H. Eur. J. Org. Chem. 1999, 959. Grossmith, C.E., Senia, F., Wagner, J. Synlett 1999, 1660. Diedrichs, N., Westermann, B. Synlett 1999, 1127. Beal, L.M., Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639.
15. For recent reviews, see: Schuster, S., Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2036. Grubbs, R.H., Miller, S.J., Fu, G. Acc. Chem. Res. 1995, 28, 446. Synthesis of Ncontaining heterocycles using RCM, see: Martin, S.F., Chen, H.J., Courtney, A.K., Liao, Y.S., Patzel, M., Ramser, M.N., Wagman, A.S. Tetrahedron 1996, 52, 7251; Pandit, U.K., Overkleeft, H.S., Borer, B.C., Bieräugel, H. Eur. J. Org. Chem. 1999, 959. Grossmith, C.E., Senia, F., Wagner, J. Synlett 1999, 1660. Diedrichs, N., Westermann, B. Synlett 1999, 1127. Beal, L.M., Moeller, K.D. Tetrahedron Lett. 1998, 39, 4639.
16. de Meijere, A., Meyer, F.E. Angew. Chem. Int. Ed. Engl. 1994, 33, 2379. Cabri, W., Candiani, I. Acc. Chem. Res. 1995, 28, 2.
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18. Lennartz, M., Sadakane, M., Steckhan, E. Tetrahedron 1999, 55, 14407.
19. +: calcd. 236.1102, found 236.1095.
20. The same type of isomerization has also been observed in other cases where enamides or enols can be formed after isomerization of the primary product: Ripa, L., Hallberg, A. J. Org. Chem. 1996, 61, 7147. Tietze, L.F., Ferraccioli, R. Synlett 1998, 145. Tenaglia, A., Karl, F. Synlett 1996, 327.
21. The same type of isomerization has also been observed in other cases where enamides or enols can be formed after isomerization of the primary product: Ripa, L., Hallberg, A. J. Org. Chem. 1996, 61, 7147. Tietze, L.F., Ferraccioli, R. Synlett 1998, 145. Tenaglia, A., Karl, F. Synlett 1996, 327.
22. The same type of isomerization has also been observed in other cases where enamides or enols can be formed after isomerization of the primary product: Ripa, L., Hallberg, A. J. Org. Chem. 1996, 61, 7147. Tietze, L.F., Ferraccioli, R. Synlett 1998, 145. Tenaglia, A., Karl, F. Synlett 1996, 327.
23. +.