Boron(III) bromide-induced ring contraction of 3-oxygenated piperidines to 2-(bromomethyl)pyrrolidines

Tetrahedron Letters

Volumn 41, Issue 14, 2000, Pages 2507-2510

  Tehrani, Kourosch Abbaspour ^a   Van Syngel, Kris ^a   Boelens, Mark ^a   Contreras, Jan ^a   De Kimpe, Norbert ^a   Knight, David W ^b  

^a Fac Agric Appl Biol Sci   (Belgium)

^b CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

Piperidines; Pyrrolidines; Ring transformation

Indexed keywords

BORON; BROMIDE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034175622     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00191-X     Document Type: Article

References (15)

1. Fuson, R. C.; Zirkle, C. L. J. Am. Chem. Soc. 1948, 70, 2760-2762.
2. Horning, D. E.; Muchowski, J. M. Can. J. Chem. 1974, 52, 1321-1330.
3. Moragues, J.; Prieto, J.; Spickett, R. G. W.; Vega, A. J. Chem. Soc., Perkin Trans. 1 1976, 938-940.
4. Black, D.; Doyle, J. E. Adv. Heterocycl. Chem. 1980, 27, 1-29.
5. Reitsema, R. H. J. Am. Chem. Soc. 1949, 71, 2041-2043.
6. Hammer, C. F.; Weber, J. D. Tetrahedron 1981, 37, 2173-2180.
7. Cossy, J.; Dumas, C.; Michel, P.; Gomez Pardo, D. Tetrahedron Lett. 1995, 36, 549-552.
8. Duhamel, L.; Poirier, J. M. Tetrahedron Lett. 1976, 2437-2440.
9. Duhamel, P.; Kotera, M. J. Org. Chem. 1982, 47, 1688-1691.
10. Donati, D.; Fusi, S.; Macripo, M.; Ponticelli, F. J. Heterocycl. Chem. 1987, 24, 481-483.
11. Plaquevent, J.-C.; Chichaoui, I. Bull. Soc. Chim. Fr. 1996, 133, 369-379.
12. De Kimpe, N.; Stevens, C.; Virag, M. Tetrahedron 1996, 52, 3303-3312.
13. De Kimpe, N.; Boelens, M.; Contreras, J. Tetrahedron Lett. 1996, 37, 3171-3174.
14. +, 2), 218/220 (18), 171 (12), 170 (22), 156 (100), 140 (18), 138 (10), 98 (10), 95 (8), 81 (12), 72 (12), 71 (19), 70 (11), 58 (21), 56 (52), 55 (21), 44 (27), 43 (43), 42 (22), 41 (35). B.p. 88-92°C/20 mmHg.
15. Suzuki, A.; Hara, S. In Encyclopedia of Reagents for Organic Synthesis; Paquette, L. A. Editor-in-chief. Boron tribromide. John Wiley & Sons: Chichester, UK, 1995; Vol. 1, pp. 645-648.