Stereoselective synthesis of hydroxypyrrolidines and hydroxypiperidines by cyclization of γ-oxygenated-α,β-unsaturated sulfones

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3379-3382

  Carretero, Juan Carlos ^a   Arrayás, Ramón Gómez ^a   De Gracia, Isabel Storch ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0343930698     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00551-5     Document Type: Article

References (19)

1. Simpkins N. S. Sulphones in Organic Synthesis, Pergamon, Oxford, 1993.
2. For two reviews, see: a) Isobe, M. Perspectives in the Organic Chemistry of Sulfur; Zwanemburg, B.; Klander, A. J. H., Ed.; Elsevier, New York, 1987, pp 209-229.
3. b) Fuchs, P. L.; Braish, T. F. Chem. Rev. 1986, 86, 903.
4. See for instance: a) Akiyama, E.; Hirama, M. Synlett 1995, 100.
5. b) De Blas J.; Carretero, J. C.; Domínguez, E. Tetrahedron Lett. 1994, 35, 4603.
6. c) Jin, Z.; Fuchs, P. L. Tetrahedron Lett. 1993, 34, 5205.
7. d) Hirama, M.; Hioki, H.; Ito, S.; Kabuto, C. Tetrahedron Lett., 1988, 29, 3121.
8. Carretero, J. C.; Gómez Arrayás R. J. Org. Chem. 1995, 60, 6000.
9. b) Ogura, K.; Kayano, A.; Fujino, T.; Sumitani, N.; Fujita, M. Tetrahedron Lett. 1993, 34, 8313.
10. Indolizidine alkaloids: Michael, J. P. Nat. Prod. Rep. 1995, 12, 535.
11. Pyrrolizidine alkaloids: Robins, D. J. Nat. Prod. Rep. 1995, 12, 413.
12. Domínguez, E.; Carretero, J. C. Tetrahedron 1990, 46, 7197.
13. In the case of 10b, 10c, 10d, 12b, 12c and 12d the cis/trans mixture could be readily separated by flash chromatography.
14. 2,3 (≈ 9.5 Hz) and NOESY spectra of trans-11 (R=H) show that both substituents at C-2 and C-3 are in equatorial positions. formula presented
15. For related intramolecular conjugate additions to γ-alkoxy-α,β-unsaturated esters see: a) Gung, B. W.; Francis, M. B. Tetrahedron Lett. 1995, 36, 2579.
16. b) Gung, B. W.; Francis, M. B. J. Org. Chem. 1993, 58, 6177.
17. c) Dai, W.; Nagao, Y. Heterocycles 1990, 30, 1231.
18. See also, a) Takao, K.; Nigawara, Y.; Nishino, E.; Takagi, I.; Maeda, K.; Tadano, K.; Ogawa, S. Tetrahedron 1994, 50, 5681.
19. b) Spellmeyer, D. C.; Houk, K. N. J. Org. Chem. 1987, 52, 959.