A Novel Approach to Substituted Pyrrolidines and Piperidines via Olefin Metathesis

Synlett

Volumn 1996, Issue 1, 1996, Pages 65-66

  Huwe, Christoph M ^a   Kiehl, Oliver C ^a   Blechert, Siegfried ^a  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0010419971     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5309     Document Type: Article

References (17)

1. For a recent review about applications of ring closing olefin metathesis see: Schmalz, H.-G. Angew. Chem. 1995, 107, 1981; Angew. Chem. Int. Ed. Engl. 1995, 34, 1833.
2. For a recent review about applications of ring closing olefin metathesis see: Schmalz, H.-G. Angew. Chem. 1995, 107, 1981; Angew. Chem. Int. Ed. Engl. 1995, 34, 1833.
3. (a) Southon, I.W.; Buckingham, J. (Ed.) Dictionary of Alkaloids; Chapman and Hall: London, 1989.
4. (b) Rubiralta, M.; Giralt, E.; Diez, A. Piperidine; Elsevier: Amsterdam, 1991.
5. (a) Junga, H.; Blechert, S. Tetrahedron Lett. 1993, 34, 3731.
6. (b) Huwe, C.M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621.
7. 13C NMR, MS, IR). Stated yields are unoptimized.
8. Fu, G.C.; Nguyen, S.T.; Grubbs, R.H. J. Am. Chem. Soc. 1993, 115, 9856.
9. Winterfeldt, E. Stereoselektive Synthese - Prinzipien und Methoden; Friedr. Vieweg & Sohn; Braunschweig, 1988.
10. Huwe, C.M.; Blechert, S., unpublished results.
11. For a recent synthesis of vinyl glycine derivatives see: Hallinan, K.O.; Crout, D.H.G.; Errington, W. J. Chem. Soc., Perkin Trans. 1 1994, 3537.
12. Huwe, C.M.; Blechert, S. Tetrahedron Lett. 1994, 35, 9537.
13. For example see: Hamada, Y.; Hara, O.; Kawai, A.; Kohno, Y.; Shioiri, T. Tetrahedron 1991, 47, 8635.
14. Commercially available L- or DL-allylglycine (2-amino-4-pentenoic acid) was used (Aldrich, Fluka).
15. Huwe, C.M.; Blechert, S. Tetrahedron Lett. 1994, 35, 9533.
16. 5 were dissolved in 4 ml of dry benzene (argon glovebox). To this solution 75 mg (0.20 mmol) (R)-N-(1-trityloxymethylallyl)-acrylamide (9) in 2 ml of dry benzene were added. After stirring for 20h at r.t. another 4.5 mg (4.9 μmol, 2.5 mol%) [Ru] were added and the solution stirred for 28h at r.t. The reaction mixture was then removed from the glovebox and flash chromatographed on silica to give 54 mg (76%) of 10c as a white foam.
17. -1] = 952 (w), 1012 (w), 1026 (w), 1073 (m), 1098 (w), 1186 (w), 1203 (m), 1241 (w), 1267 (w), 1309 (w), 1382 (w), 1417 (s), 1451 (w), 1478 (w), 1675 (w), 1775 (vs), 2858 (w), 2916 (w), 2931 (w), 2975 (w).