A [3+2] Annulation Procedure for the Synthesis of Bicyclic Methylenepyrrolidines

Synlett

Volumn 1997, Issue 1, 1997, Pages 95-96

  Sadakane, Masahiro ^a   Vahle, Ruth ^a   Schierle, Kerstin ^a   Kolter, Doris ^a   Steckhan, Eberhard ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0008697109     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-691     Document Type: Article

References (17)

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2. (b) Knapp, S.; O'Connor, U.; Mobilio, D. Tetrahedron Lett. 1980, 21, 4557.
3. (c) D'Aniello, F.; Mattii, D.; Taddei, M. Synlett 1993, 119.
4. (a) Steckhan, E.; Zietlow, A.; Herborn, C. Angew. Chem. Int. Ed. Engl. 1989, 28, 1399.
5. (b) Steckhan, E.; Brungs, P.; Zietlow, A.; Stahl, A.; Lewall, B.; Kardassis, G.; Papadopoulos, A. in : Modern Methodology in Organic Synthesis, Shono, T. Ed.; Kodansha. VCH, Tokyo, Weinheim 1992; p 323.
6. (c) Stahl, A.; Steckhan, E.; Nieger, M. Tetrahedron Lett. 1994, 35, 7371.
7. (d) Zietlow, A.; Steckhan, E. J. Org. Chem. 1994, 59, 5658.
8. (e) Brungs, P.; Danielmeier, K.; Jakobi, J.; Nothhelfer, C.; Stahl, A.; Zietlow, A.; Steckhan, E. J. de Chimie Physique 1996, 93, 575. Danielmeier, K.; Schierle, K.; Steckhan, E. Angew. Chem. Int. Ed. Engl. 1996, 35, 2247.
9. (e) Brungs, P.; Danielmeier, K.; Jakobi, J.; Nothhelfer, C.; Stahl, A.; Zietlow, A.; Steckhan, E. J. de Chimie Physique 1996, 93, 575. Danielmeier, K.; Schierle, K.; Steckhan, E. Angew. Chem. Int. Ed. Engl. 1996, 35, 2247.
10. 3, 100.6 MHz) δ 20.86, 29.28, 30.98, 40.68, 49.42, 59.09, 107.41, 142.83, 168.61.
11. Danielmeier, K.; Schierle, K.; Steckhan, E. Tetrahedron 1996, 52, 9743.
12. The coupling constants between C4-C5 of 3d and 3e are 3.0 Hz and 4.4 Hz, respectively. The trans configurations were also confirmed by NOE experiments. The diastereoselectivities were determined by gas chromatography.
13. 1H-NMR.
14. Louwrier, S.; Ostendorf, M.; Boom, A.; Hiemstra, H.; Speckamp, W. N. Tetrahedron 1996, 52, 2603.
15. 1H-NMR.
16. The PMB group was cleaved with CAN in 80 % yield. The cyclization of 3g with NaH in THF failed. (Equation Presented)
17. 2h and 2i were used without purification after electrochemical generation.