Radical cyclisation of amino aldehydes leading to hydroxy pyrrolidines and piperidines

Tetrahedron Letters

Volumn 38, Issue 33, 1997, Pages 5907-5910

  Parsons, Andrew F ^a   Pettifer, Robert M ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030839955     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01316-6     Document Type: Article

References (19)

1. Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K.J.; Trach, F. Organic Reactions 1996, 48, 301.
2. Enholm, E.J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939; Enholm, E.J.; Burroff, J.A. Tetrahedron Lett. 1992, 33, 1835.
3. Enholm, E.J.; Prasad, G. Tetrahedron Lett. 1989, 30, 4939; Enholm, E.J.; Burroff, J.A. Tetrahedron Lett. 1992, 33, 1835.
4. s see: Hays, D.S.; Fu, G.G. J. Org. Chem. 1996, 61, 4.
5. Enholm, E.J.; Kinter, K.S. J. Am. Chem. Soc. 1991, 113, 7784; Enholm, E.J.; Kinter, K.S. J. Org. Chem. 1995, 60, 4850.
6. Enholm, E.J.; Kinter, K.S. J. Am. Chem. Soc. 1991, 113, 7784; Enholm, E.J.; Kinter, K.S. J. Org. Chem. 1995, 60, 4850.
7. See for example: Goodall, K.; Parsons, A.F. Tetrahedron Lett. 1997, 38, 491; Parsons, A.F.; Taylor, R.J.K. J. Chem. Soc., Perkin Trans. 1 1994, 1945.
8. See for example: Goodall, K.; Parsons, A.F. Tetrahedron Lett. 1997, 38, 491; Parsons, A.F.; Taylor, R.J.K. J. Chem. Soc., Perkin Trans. 1 1994, 1945.
9. 2: Baldwin, J.E.; MacKenzie Turner, S.C.; Moloney, M.G. Tetrahedron 1994, 50, 9411 and 9425; Using Mg: Lee, G.H.; Choi, E.B.; Lee, E.; Pak, C.S. J. Org. Chem. 1994, 59, 1428.
10. 2: Baldwin, J.E.; MacKenzie Turner, S.C.; Moloney, M.G. Tetrahedron 1994, 50, 9411 and 9425; Using Mg: Lee, G.H.; Choi, E.B.; Lee, E.; Pak, C.S. J. Org. Chem. 1994, 59, 1428.
11. For a similar electroreduction reaction see: Shono, T.; Nishiguchi, I.; Ohmizu, H.; Mitani, M. J. Am. Chem. Soc. 1978, 100, 545.
12. For a review of the preparation and transformations of α-amino aldehydes see: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
13. The concentration of the reaction was 0.1 M. Increasing the concentration (e.g. to 0.5 M) has been shown to afford 1,2-pinacol byproducts in related systems (see ref. 2).
14. For slow cyclisation reactions further AIBN was added until all the starting material had been consumed.
15. All new compounds exhibited satisfactory spectral and analytical (high resolution mass and/or combustion) data. Yields are of pure isolated product and are not optimised.
16. 3SnH.
17. Considerably lower yields of (14) and (15) were isolated using crude alkene (12) or (13).
18. 13C) showed the formation of only one lactone diastereomer and this was assigned to be the cis-isomer.
19. .3 group in both compounds.